Category: 366-99-4

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 366-99-4 as follows. SDS of cas: 366-99-4

Example 18; Synthesis of (4-Chloro-6-cyclohexylmethoxy-[1,3,5]triazin-2-yl)-(3-fluoro-4-methoxy-phenyl)-amine (114); To a sample of 113 (1.011 g, 3.8 mmol) dissolved in acetone (20 mL) was added a solution of 3-fluoro-p-anisidine (0.541 g, 3.8 mmol) in acetone (10 mL) followed by addition of NaOH (1.52 mL, 2.5 N, 3.8 mmol) and water (3 mL). The reaction mixture was allowed to stir at reflux for about 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine solution and dried over potassium carbonate. The sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (silica gel, 70:30 hexanes:ethyl acetate) yielded light yellow solid compound 114 (0.581 g, 42percent), mp 98° C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.36; MS (ESI): m/z 369 (39.1), 368 (22.1), 367 (M+H, 100), 273 (3.2), 271 (10.7).; Example 19; 6-Cyclohexylmethoxy-N,N’-bis-(3-fluoro-4-methoxy-phenyl)-1,3,5-triazine-2,4-diamine; Compound 115 was obtained as a by-product (0.159 g) via column chromatography (silica gel, 70:30 hexanes:ethyl acetate), mp 181° C.; TLC (silica gel, 30:70 ethyl acetate:hexanes), Rf 0.17; MS (ESI): m/z 472 (M+H, 100), 261 (1.5).

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209881; (2004); A1;,
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Application of 366-99-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Acetic anhydride (159 mmol, 1 .495 eq) is added to 3-fluoro-4-methoxyaniline (106 mmol, 1 eq) at RT and the resulting mixture is stirred at this temperature for 30 minutes. Nitric acid (156 mmol, 1.57 eq) is then added dropwise and the resulting suspension is stirred at RT for 3 h. Water is added to quench the reaction, the resulting solid collected by filtration and dried under vacuum. A/-(5-Fluoro-4-methoxy-2-nitrophenyl)acetamide (24.2 g) is obtained as a yellow solid. LC-MS (conditions F): tR = 0.71 min, [M + 1 + CH3CN]+ = 270.25.

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOSS, Christoph; BROTSCHI, Christine; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi T.; WO2012/85857; (2012); A1;,
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Reference of 366-99-4, These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Was added in a 500 mL reaction flask3-fluoro-4-methoxyaniline(30 g, 0.21 mol) and dichloromethane(100 mL).The ice bath was cooled to below 5 ° C,Acetic anhydride was slowly added dropwise(22 mL, 0.23 mol),The temperature of the reaction solution was controlled at 30 ° C or lower,About 1 hour period.Remove the ice bath,After stirring at room temperature for 5 hours,N-Hexane (300 mL) was added to the reaction solution,A large number of solid precipitation.After stirring for 1 hour,The filter cake was washed with n-hexane,30 degrees vacuum drying,To give the title compound (whiteColor solid powder, 28 g, 72percent).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhang, Ruihao; (36 pag.)CN105949178; (2016); A;,
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Reference of 366-99-4, These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To cyanuric chloride (0.180 g,1 mmol) in 1,4-dioxane (1 mL) at about- 10 to-20 C was addedN, N-diisopropylethylamine (DIEA) (0.19 mL,lmmol) in CH3CN (1 mL) and3-fluoro-p-anisidine (0.14 g, 1 mmol) inCH3CN(1 mL) and stirred for about1 hour. The reaction mixture was then stirred at room temperature for about I hour. Then a solution of cycloheptylamine (0.13mL,1 mmol) and DIEA (0.19 mL, 1 mmol) inCH3CN (0.5 mL) was added and the reaction mixture was stirred overnightat rt. Then, N-methyl-4 (methylamino) piperidine (0.15 mL,1 mmol) and DIEA (0.19 mL,1 mmol) inCH3CN (0.5 mL) were added and the reaction mixture was refluxed overnight. The reaction mixture was worked-up using saturated sodium bicarbonate, and brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 90: 9: 1 dichloromethane: methanol:conc. ammonium hydroxide) to give 158 (0.130 g, 28percent) ; TLC (silica gel, 90: 9 : 1,CH2CI2, CH30H, conc.NH40H), Rf 0.26) ;1H NMR (600MHz, CDC13, 55 C)8 7.74 (br s, 1H), 6.94 (br s, 1H), 6.81-6. 84(m, 2H), 4.83 (br resonance, 1H), 4.55 (s,1H), 3.98 (s,1H), 3.82 (s,3H), 2.97 (s, 3H), 2.94 (br d,J=11. 9 Hz, 2H), 2.29 (s, 3H), 2.06-2. 10(m, 2H), 1.93-1. 97(m, 2H), 1.84-1. 90(m, 2H), 1.44-1. 66(m, 12H). Compound 159 was’isolated as a by-product (55 mg) by column chromatography (silica gel, 90: 9: 1 dichloromethane: methanol:conc. ammonium hydroxide); TLC (silica gel, 90: 9: 1,CH2C12, CH30H, conc.NH40H), Rf 0.1) ; HPLC: Inertsil ODS-3V C18, 40: 30: 30 [KH2PO4(0. 01 M, pH 3.2) :CH30H : CH3CN], 264nm, Rt 8.3 min, 93.5percent purity; MS(ESp : m/z 443 (M+H, 100).

Statistics shows that 3-Fluoro-4-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 366-99-4.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: ethers-buliding-blocks

To a stirred light brown solution of 10.0 g (49.6 mmol) 3-Fluoro-4-methoxy aniline in 56 ml DCM was added rapidly a solution of 4.38 g (52 mmol, 1.05 eq.) NaHCO3 in 70 ml of water. To the resulting biphasic mixture was added under vigorous stirring 5.72 ml (74.4 mmol, 1.5 eq.) methyl chloroformate over a period of 30 min. The light brown reaction mixture was stirred for 1.5h at RT. The organic phase was separated and washed twice with a total amount of 50 ml water, and the combined aqueous phases were washed twice with a total amount of 100 ml DCM. The combined organic phases were dried over 2 g Na2SO4 and filtered with suction on a funnel with a fritted disk. The cake was washed in total with 50 ml DCM. The DCM was partially removed under reduced pressure to about 1/3 of its original volume and then 70 ml heptane was added dropwise under stirring within 30 min, whereby the product precipitated. From this suspension, DCM was completely removed under reduced pressure. Finally, the suspension was stirred in an ice bath for 1h, the crystals were filtered off with suction on a funnel with a fritted disk and washed with three 10 ml portions, in total with 30 ml ice cold heptane. The wet off-white crystals were dried at 50°C in vacuo to yield 9.65 g (97.7percent of theory) of the title compound as off-white crystals (m.p. = 96.1-96.5°C) 1H-NMR data (CDCl3, 300 MHz): delta 7.29 (m, 1H), 6.98 (m, 1H,), 6.89 (dd, 1H), 6.44 (br s, 1H), 3.86 (s, 3H), 3.77 (s, 3H). MS m/e (percent): 200 ([M+H]+, 100).

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. Hoffmann-La Roche AG; EP2011783; (2009); A1;,
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Synthetic Route of 366-99-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 4a (see general route 4, procedure H, M and K)2-(3-fluoro-4-methoxyphenyl)hydrazine; [00257] A room temperature solution of 3-fluoro-4-methoxyaniline (25.0 g, 177 mmol) in concentrated 12M aqueous hydrochloric acid solution (60 mL) was stirred for two hours, after which it was cooled to 0°C to which a solution of sodium nitrite (14.2 g, 205 mmol), in water (50 mL), was added, drop-wise over 45 minutes, with internal temperature monitoring such that the reaction temperature does not warm above 5°C. After stirring for one hour at 0°C, the reaction mixture was poured slowly into a 0°C pre-made solution of tin(II) chloride dihydrate (168 g, 744 mmol) in concentrated 12M aqueous hydrochloric acid solution (125 mL). The reaction mixture was allowed to warm up to room temperature, after which it was stored in the freezer overnight (12 hours), leading to the formation of a precipitate. This dark brown solid was successively washed with water (2 x 100 mL) and diethyl ether (3 x 100 mL), and dried to afford crude 2-(3-fluoro-4-methoxyphenyl)hydrazine hydrochloride as a pasty brown solid (note that this crude solid can also be used directly in the next step). As part of the purification and isolation process, the crude hydrazine hydrochloride salt was reconstituted in water (100 mL) and 3M aqueous sodium hydroxide solution (200 mL), extracted with diethyl ether (2 x 200 mL), washed with successively with saturated sodium bicarbonate solution (2 x 100 mL), water (2 x 20 mL) and saturated sodium chloride solution (2 x 20 mL), dried (sodium sulfate), filtered and concentrated to afford 2-(3-fluoro-4- methoxyphenyl)hydrazine as a light yellow solid (15.0 g, 96.1 mmol, 54percent yield. 1H NMR (400 MHz, CDC13) delta (ppm): 6.87 (m, 1H), 6.66 (dd, 1H), 6.49-6.53 (m, 1H), 5.06 (br. s, 1H), 3.83 (s, 3H), 3.55 (br. s, 2H).[00258] A portion of 2-(3-fluoro-4-methoxyphenyl)hydrazine (5.00 g, 32.0 mmol) was dissolved in absolute ethanol (50 mL), to which a solution hydrogen chloride (15 mL, 2.5M in ethanol) was added. The resulting precipitate was filtered, washed with ethyl acetate (2 x 40 mL), and dried to afford 2-(3-fluoro-4-methoxyphenyl)hydrazine hydrochloride as an off- white solid (4.7 g).

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
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Synthetic Route of 366-99-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 366-99-4 as follows.

2-pentanone (17.2 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydnde (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stined at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford 3-Fluoro-4-methoxy-N-(pentan-2-yl)aniline(2.1 g, 50percent yield). MS m/z=212 [M+H].

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JIANGSU ASCENTAGE BIOMED DEVELOPMENT INC.; CHEN, Jianyong; ZHOU, Yunlong; WANG, Shaomeng; GUO, Ming; YANG, Dajun; JIAO, Lingling; JING, Yu; QIAN, Xu; LIU, Liu; BAI, Longchuan; YANG, Chao-Yie; MCEACHERN, Donna; WO2015/127629; (2015); A1;,
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Ether | (C2H5)2O – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Fluoro-4-methoxyaniline

Under room temperature, will 3-fluoro-4-anisidine (21.0 g, 0 . 15 mol) adding water in (100 ml). To the stirring mixture of lowering the temperature to -5 to 0 °C. To the obtained sequentially adding in a mixture of concentrated hydrochloric acid (45 ml), sodium nitrite solution (70 ml), 2-chloro-3-oxo butyric acid ethyl ester (24.7 g, 0 . 15 mol) of ethanol solution (150 ml) and sodium acetate (36.9 g, 0 . 45 mole) aqueous solution (150 ml). After the completion of the dropping, the obtained mixture of low-temperature stirring 0.5 hours. Furthermore, the obtained mixture to room temperature, stirring for 6 hours, a solid precipitated in the reaction process. After the completion of the reaction, the obtained by filtering the mixture. The filter cake obtained by vacuum drying, the silica gel column chromatography (PE:EA=10:1) product is obtained by purification of 36.5 g (yield: 88.6percent).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 366-99-4.

Reference:
Patent; CSPC Weisheng Pharmaceutical Technology (Shijiahuang) Co., Ltd.; Shi, Ying; Gao, Qingzhi; Mi, Yi; Wang, Xuliang; (129 pag.)CN105384739; (2016); A;,
Ether – Wikipedia,
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Synthetic Route of 366-99-4,Some common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 62; Synthesis of N,N’-dicyclopropyl-N-(3-fluoro-4-methoxy-phenyl)-1,3,5-triazine-2,4,6-triamine (157); To cyanuric chloride (0.368 g, 2 mmol) in CH3CN at about -20° C. was added 3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of DIEA (0.39 mL, 2.2 mmol) and stirred for about I hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then cyclopropylamine (1.39 mL, 20 mmol) and DIEA (0.39 mL, 2.2 mmol) were added and the reaction mixture was stirred overnight at rt. The reaction mixture was worked up as usual, diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, concentrated under reduced pressure, and compound 157 was purified by silica gel column chromatography (200 mg, 30percent), mp 91-92° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 8.6 min, 99.1percent purity; MS (ESI): m/z 331(M+H, 100), 305 (0.8), 151 (0.3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluoro-4-methoxyaniline, its application will become more common.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 366-99-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-butanone (14.40 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford N-(sec-Butyl)-3-fluoro-4-methoxyaniline (2.6 g, 66percent yield). MS m/z=198 [M+H].

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Fluoro-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.