Category: 366-99-4

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 366-99-4, name is 3-Fluoro-4-methoxyaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8FNO

Example 104 Synthesis of 6-Chloro-N,N’-bis-(3-fluoro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine (E15) To 124 (1.09 g, 3.5 mmol) dissolved in acetone (25 mL) was added 3-fluoro-p-anisidine (0.54 g, 3.5 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.4 mL, 3.5 mmol) and water (3.5 mL). The reaction mixture was stirred and heated at reflux for 3 hours. The reaction mixture was extracted three times using dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was filtered, concentrated in vacuo, and the resulting solid was dried overnight under vacuum to yield white solid (E15) (1.332 g, 97percent); mp 194° C.; HPLC: Inertsil ODS 3V C18, 40:30:30 v:v:v [KH2PO4 (0.01 M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 33.2 min, 97.6percent purity; MS (TOF ES+) m/z 396 (35.0); 394 (M+H, 100).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Reddy, Velagala Venkira Rama Murali Krishna; Sridevi, Bhatlapenumarphy Shesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/224950; (2004); 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 31 Synthesis of (4,6-Dichloro-[1,3,5]triazin-2-yl)-(3fluoro-4-methoxy-phenyl)-amine (124) To cyanuric chloride (28.84 g, 156.0 mmol) dissolved in acetone (200 mL) stirring at approximately 0-5° C., was added a solution of 3-fluoro-p-anisidine (22.16 g, 156.0 mmol) in acetone (200 mL) followed by the addition of NaOH (63 mL, 2.5 N, 156.0 mmol). The reaction mixture was allowed to stir at approximately 0-5° C. for about 2 hours. The reaction mixture was then poured over crushed ice and neutralized with 10percent HCl (aq) and 5percent NaOH (aq). The resulting solid was collected by vacuum filtration, washed with water and dried overnight under vacuum. Column chromatography (silica gel, 70:30 hexane:ethyl acetate) yielded light yellow solid compound 124 (29.6 g, 66percent); mp 134° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 20.3 min, 97.7percent purity.

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.

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

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. Application In Synthesis of 3-Fluoro-4-methoxyaniline

To a mixture of cyanuric chloride (0.368 g, 2 mmol) inCH3CN atabout-20 C was added3-fluoro-p-anisidine (0.28 g, 2 mmol) inCH3CN followed by the additionof N, N-diisopropylethylamine (DIEA) (0.35 mL, 2 mmol) and stirred for about 1 hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then, cyclohexylmethyl amine (0.26mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at RT. Then, S-(-)- 2-aminomethyl-N-ethyl pyrrolidine (0.29 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced. The crude material was purified by column chromatography eluting with 96: 3: 1 methylene chloride: methanol: cone. ammonium hydroxide to yield a white solid 141 (0.400 g, 43.7percent), mp68-69 OC ; HPLC: Inertsil ODS-3V C18, 40: 30: 30[KH2P04(0. 01 M, pH3. 2) :CH30H : CH3CN], 264nm, Rt 8.2 min, 97.1percent purity ; MS (ESI):lnlz 458 (M+H, 100), 362 (2.8), 230(85. 4).

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

366-99-4, name is 3-Fluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 366-99-4

Reference Example 13; N- (5-Fluoro-4-methoxy-2-nitrophenyl) acetamide; Acetic anhydride (5 ml) was added to 3-fluoro-4- methoxyaniline (5.0 g), and the mixture was stirred for 30 minutes. The reaction mixture was cooled to room temperature, and nitric acid (2.3 ml) was added dropwise thereto. The mixture was stirred for 30 minutes, and water was added thereto. The resulting precipitate was collected and washed with water to obtain the title compound as crystals (5.7 g, 71percent). H-NMR (300 MHz, CDC13) 5 (ppm): 2.29 (3H, s), 3.94 (3H, s), 7.80 (1H, d, J=8. 4Hz), 8.66 (1H, d, J=10.5Hz), 10.39 (1H, brs).

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/82879; (2005); A1;,
Ether – Wikipedia,
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., category: ethers-buliding-blocks

Cyclohexanone (19.62 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-Cyclohexyl-3-fluoro-4-methoxyaniline (2.8 g, 63percent yield). MS m/z=224 [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;,
Ether – Wikipedia,
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., SDS of cas: 366-99-4

General procedure: To a solution of compound 12 (bakuchiol-o-triflate) (1 mmol) in toluene (10 mL M), amine (3.0 mmol), Cs2CO3 (4.0 mmol), ligand (±) BINAP (0.6 mol) and Pd(OAc)2 (0.2 mol) were added under an inert atmosphere. The reaction mixture was degassed at RT and refluxed (120 °C) for 24 hr. Then, the reaction mixture was brought to RT, diluted with EtOAc and filtered through celite. To the reaction mixture, brine (20 mL) was added and extracted with EtOAc (2 × 10 mL). The combined organic layerwas dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford the product after silicagel chromatography purification (Hex/EtOAc, 9.5:0.5).

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:
Article; Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 75 – 80;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 366-99-4, A common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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.

Step 1. To a mixture of 3-fluoro-4-methoxyaniline (3.00 g, 21.3 mmol) and paraformaldehyde (1.28 g, 42.5 mmol) in MeOH (100 mL) was added sodium methoxide (19.4 mL, 85.0 mmol) and the reaction mixture mixture was sealed and heated at 55 °C for 2 h. After cooling to rt, sodium borohydride (2.01 g, 53.1 mmol) was added in small portions. The final reaction mixture was stirred at rt overnight. The solvent was removed in vacuo and the residue was taken up in EtOAc (100 mL) and washed with water (150 mL). The separated aqueous component was saturated with NaCl, extracted with EtOAc (100 mL) and the combined organic components were washed with brine (50 mL), dried over MgS04, filtered, and concentrated in vacuo. The residue was taken up into DCM (10 mL) and purified by FCC (80 g silica gel cartridge), eluting with gradient 5percent~50percent EtO Ac- hexanes to afford 3-fluoro-4-methoxy-N-methylaniline (3.08 g) as a light yellow oil. LC- MS retention time = 1.34 min; m/z = 153.42 [M-H]-. (Start percent B = 0, Final percent B = 100, Gradient Time = 2 min, Flow Rate = 1 ml/min, Wavelength = 220, Solvent Pair = Water: Acetonitrile 10 mM Ammonium Acetate, Solvent A = 95percent Water: 5percent Acetonitrilel 10 mM Ammonium Acetate, Solvent B = 5percent Water: 95percent Acetonitrile 10 mM Ammonium Acetate, Column = Phenomenex Luna CI 8 2.0 X 30mm 3um, MW1 = 132+/- Oven Temp. = 40 °C).

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

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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.

Cyclopentanone (16.8 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-Cyclopentyl-3-fluoro-4-methoxyaniline (2.0 g, 48percent yield). MS m/z=210 [M+H].

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

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 366-99-4, name is 3-Fluoro-4-methoxyaniline, A new synthetic method of this compound is introduced below., Quality Control of 3-Fluoro-4-methoxyaniline

Acetone (11.6 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 3-Fluoro-N-isopropyl-4-methoxyaniline (2.90 g, 79percent yield). 1H NMR (400 MHz, CDC13) delta ppm 6.84 (dd, J= 9.5, 8.7 Hz, 1H), 6.41 (dd, J= 13.5, 2.7 Hz, 1H), 6.33- 6.27(m, 1H), 3.83 (s, 3H), 3.54-3.52(m, 1H), 3.28 (s, 1H), 1.21 (d, J= 6.3 Hz, 6H).

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

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;,
Ether – Wikipedia,
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., HPLC of Formula: C7H8FNO

To cyanuric chloride (28.84 g, 156.0 mmol) dissolved in acetone (200 mL) stirring at approximately 0-5 C, was added a solution of 3-fluoro-p-anisidine (22.16 g, 156.0 mmol) in acetone (200 mL) followed by the addition of NaOH (63 mL, 2.5 N, 156.0 mmol). The reaction mixture was allowed to stir at approximately 0-5 C for about 2 hours. The reaction mixture was then poured over crushed ice and neutralized with 10percent HCI(aq) and 5percent NaOH(aq). The resulting solid was collected by vacuum filtration, washed with water and dried overnight under vacuum. Column chromatography (silica gel, 70: 30 hexane: ethyl acetate) yielded light yellow solid compound 124 (29.6 g, 66percent); mp 134 C ; HPLC: Inertsil ODS-3V C18,40 : 30: 30[KH2PO4(O. 01M, pH 3.2) :CH30H : CH3CN], 264nm, Rt 20.3 min, 97.7 percent purity.

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