Author: Jessica.F

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. 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6851-80-5

General procedure: To a mixture of the corresponding secondary amines 14A-F (0.6 mmol), anhydrous K2CO3 (89.7 mg, 0.65 mmol) and KI (8.6 mg, 0.052 mmol) in anhydrous CH3CN (12 ml) were added the appropriate intermediates 10-13 (0.5 mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in water (40 mL) and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of CH2Cl2/CH3OH (100:1) as eluent to afford the corresponding scutellarein-O-alkylamine derivatives 15-18.

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 6851-80-5.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Yuan, Wen; Liu, Qiang; Shi, Yikun; Ang, Wei; Luo, Youfu; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 348 – 366;,
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162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, 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. COA of Formula: C18H21NO4

Example 2 (Z)-1-(2-bromo-3,4,5-trimethoxyphenyl)-3-((2-methoxy-5-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)prop-2-en-1-one (10y) To a stirred solution of (Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)aniline (5d) (100 mg, 0.317 mmol) in ethanol (5 ml) 1-(2-bromo-3,4,5-trimethoxyphenyl)prop-2-yn-1-one (6y) (94.9 mg, 0.317 mmol) was added. The reaction mixture was stirred at a temperature of 27 C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (1:1) as a solvent system. Then water (10 ml) was added to reaction mixture. A yellow colour solid appears which was filtered and washed with ethanol. (yield: 150 mg, 76%); mp: 108-110 C.; 1H NMR (CDCl3, 300 MHz) deltadelta (ppm): 3.94 (s, 3H), 3.91 (s, 3H), 3.90 (s, 3H), 3.87 (s, 3H), 3.84 (s, 3H), 3.70 (s, 6H), 5.64 (d, J=8.30 Hz, 1H), 6.49 (d, J=9.06 Hz, 4H), 6.81 (d, J=8.3 Hz, 1H), 6.87 (s, 1H) 6.97 (d, J=8.3 Hz, 1H), 7.14 (s, 1H), 7.28-7.19 (m, 1H), 11.92 (d, J=12.8 Hz, NH); FABMAS: (M+H)=614.

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Council of Scientific and Industrial Research; Ahmed, Kamal; Gajjela, Bharath Kumar; Anver, Basha Shaik; Vangala, Santhosh Reddy; Mahesh, Rasala; US2015/322009; (2015); A1;,
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Related Products of 14804-31-0,Some common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, 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.

(RS)-1-(3-Bromo-2-fluorophenyl)-1-(4-methoxy-3-methylphenyl)ethanol Magnesium turnings (981 mg) and a crystal of iodine were suspended in tetrahydrofuran (10 mL) at room temperature. To this was added ~5 mL of a solution of 4-bromo-2-methylanisole (7.1 g) in tetrahydrofuran (100 mL). The mixture was then heated at reflux until initiation (colour change from brown to colourless ~15-30 min) after which time the heat was removed. The remaining 4-bromo-2-methylanisole solution was added dropwise to maintain a gentle reflux and the resultant mixture was then heated at reflux for 2 h. Upon cooling to room temperature, a solution of 1-(3-bromo-2-fluorophenyl)-ethanone (7.3 g) in tetrahydrofuran (100 mL) was added dropwise, again maintaining a gentle reflux and this was then heated at reflux for 2 h before being allowed to cool to room temperature. The mixture was then poured onto ice-water (400 mL) and the solvent removed by evaporation. The product was extracted with ethyl acetate (3*100 mL), dried over sodium sulfate and the solvent removed by evaporation to yield a yellow oil. Purification by flash chromatography on silica (20:1-5:1 hexanes/ethyl acetate) yielded (R,S)-1-(3-bromo-2-fluorophenyl)-1-(4-methoxy-3-methylphenyl)ethanol as a yellow oil (6.37 g, 56%). 1H NMR (CDCl3): 1.94 (3H, s, ArCH3), 2.17 (3H, s, ArCH3), 3.80 (3H, s, ArOCH3), 6.75 (1H, d, Ar), 7.00-7.16 (3H, m, Ar), 7.47 (1H, t, Ar), 7.63 (1H, t, Ar).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methoxy-2-methylbenzene, its application will become more common.

Reference:
Patent; Andreini, Matteo; Gabellieri, Emanuele; Guba, Wolfgang; Marconi, Guido; Narquizian, Robert; Power, Eoin; Travagli, Massimiliano; Woltering, Thomas; Wostl, Wolfgang; US2009/209529; (2009); A1;,
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Reference of 25245-34-5, 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 25245-34-5 as follows.

General procedure: The Suzuki reaction was performed in a 50 mL round-bottomed flask, aryl halide (0.5 mmol), arylboronic acid (0.65 mmol), K2CO3 (1 mmol), Complex 1 (0.2-1 mol%) and water (4 mL) were charged and stirred for the required time at room temperature for aryl bromides or at 100 C for aryl chlorides. After completion, the mixture was cooled down to room temperature, diluted with water (10 mL) and extracted with diethyl ether (3 × 15 mL). The organic layer was washed with brine (3 × 15 mL), dried over anhydrous Na2SO4. The crude products were chromatographed on silica gel (ethyl acetate/hexane).

According to the analysis of related databases, 25245-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shahnaz, Nasifa; Puzari, Amlan; Paul, Bidisha; Das, Pankaj; Catalysis Communications; vol. 86; (2016); p. 55 – 58;,
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Synthetic Route of 1579-40-4, 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 1579-40-4 as follows.

An H-shaped reactor with two reaction chambers was purged with argon. A stirring bar (1.0 mm × 0.4 mm) was then located in each chamber of the reactor. Sulfuric acid (0.8 mL, 1.47 g, 15.0 mmol) was placed at the bottom of one chamber (chamber 1) of the reactor, and Galden HT-135 (1.0 mL) was slowly added to chamber 1 using a syringe. Subsequently, ammonium formate (443 mg, 7.0 mmol) was added, which formed a third layer in chamber 1. A solution of di-p-tolyl ether (13, 198.6 mg, 1.0 mmol), Pd(OAc)2 (5.5 mg, 2.5 mol%), and K2S2O8 (541.0 mg, 2.0 mmol) in trifluoroacetic acid (2.5 mL) was placed in the other chamber (chamber 2) of the reactor. Rubber septa were fitted to the reactor, and a needle equipped with a balloon was then pricked into the septum of chamber 2. The air in the reactor was withdrawn using a syringe until the balloon was completely flattened. The reactor was the heated in an oil bath at 45 C for 5 h under slow stirring, with care taken not to mix the layers in chamber 1, then allowed to cool to 25 C. The mixture in chamber 2 was transferred to an Erlenmeyer flask containing water using dichloromethane (DCM). The organic layer was separated, and the aqueous layer was extracted with DCM. The combined organic layers were washed with brine then dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica-gel column chromatography using hexane/chloroform (1/4) as the eluent to afford desired product, 2,7-dimethylxanthen-9-one (14, 178.8 mg, 80%) as a white solid. 2,7-Dimethylxanthen-9-one (14) [S14] OCO2MeO S11 1H-NMR (400 MHz, CDCl3): delta 8.12 (2H, d, J = 0.9 Hz, ArH), 7.53 (2H, dd, J = 8.5, 2.1 Hz, ArH), 7.39 (2H, d, J = 8.7 Hz, ArH), 2.47 (6H, s, CH3); 13C-NMR (100 MHz, CDCl3): delta 177.36, 154.42, 135.94, 133.48, 126.02, 121.43, 117.75, 20.89.

According to the analysis of related databases, 1579-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Adachi, Yusuke; Matsubara, Hiroshi; Journal of Fluorine Chemistry; vol. 216; (2018); p. 89 – 95;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1663-61-2, Application In Synthesis of (Triethoxymethyl)benzene

EXAMPLE III 1,5-diacetyl-3-(ethoxy-phenyl-methylidene)-2-indolinone 32.6 g (150 mmol) 1,5-diacetyl-2-indolinone are suspended in 100 ml triethyl orthobenzoate and stirred overnight with 150 ml acetic anhydride at 110° C. Then a further 50 ml triethyl orthobenzoate are added and the mixture is stirred for a further 24 h. Then it is evaporated down and the resulting precipitate is suction filtered, washed and dried. Yield: 38 g (72.5percent of theory) Rf=0.60 (silica gel, methylene chloride/methanol 30:1) C21H19NO4 (MW=349.384) Mass spectrum: m/z=350 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Triethoxymethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/234120; (2005); A1;,
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Electric Literature of 13468-02-5,Some common heterocyclic compound, 13468-02-5, name is N,N-Dimethyl-2-phenoxyethanamine, molecular formula is C10H15NO, 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.

The oil XI 132g (0.8mol), 30% concentrated hydrochloric acid 195g (1.6mol) was dissolved in 400ml of water with stirring, at -10 temperature or less, 40% formaldehyde was slowly added dropwise a solution of 40g (0.8mol) reaction was continued for 2 hours; TLC monitoring completion of the reaction, the pH was adjusted to 8 with sodium carbonate to 9, and extracted twice with dichloromethane, organic phases were combined and concentrated to give an oil, 300ml ethyl acetate was added to dissolve,Was added dropwise 30% HCl / ethanol, precipitated crystals were filtered to give 112.7g compound XII, a yield of 56.3%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N,N-Dimethyl-2-phenoxyethanamine, its application will become more common.

Reference:
Patent; Weihai Di Su Pharmaceutical Co., Ltd.; Wu, Ronggui; Jiang, Kai; An, Donghua; Cui, Yangyang; Men, Lianbin; (7 pag.)CN105985257; (2016); A;,
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Synthetic Route of 6298-96-0, A common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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 a 250 mL RBF was added (S)-1-(4-methoxyphenyl)ethanamine (6.24 ml, 42.3 mmol), 1-(5- methylpyridin-2-yl)ethanone (6.0 g, 44.4 mmol), DCM (Volume: 106 ml) and STAB-H (17.92 g, 85 mmol) at rt and the reaction was stirred for 24h. The reaction was quenched by the addition of 1N NaOH until a pH of 8 was achieved. The phases were separated and the organic layer was treated with 1N NaOH until pH 11 was observed. The DCM layer was dried with MgSO4, filtered and concentrated to an oily residue. The residue was purified via combiflash to separate the diastereomers (~4:1 by crude NMR, 80g column 10-30% EtOAc in hexanes, over 40 min). The fractions were concentrated to a clear oil which was crystallized using hexanes (S)-1-(4-methoxyphenyl)-N-((S)-1-(5-methylpyridin-2-yl)ethyl)ethanamine (5.1 g, 18.86 mmol, 45 % yield). 1H NMR (400 MHz, CDCl3): delta= 8.40 (d, J= 2.1 Hz, 1H), 7.39 (ddd, J= 7.8, 2.4, 0.8 Hz, 1H), 7.15 (d, J= 8.5 Hz, 2H), 6.93 (d, J= 8.1 Hz, 1H), 6.83 (d, J= 8.5 Hz, 2H), 3.78 (s, 3H), 3.53 (q, J= 6.8 Hz, 1H), 3.37 (q, J= 6.6 Hz, 1H), 1.26 (d, J= 6.4 Hz, 3H), 1.24 (d, J= 6.5 Hz, 3H); LC/MS 75% MeOH in H2O over 3 minutes, rt = 0.480 at 254 nM, MS (+) 271.2.

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; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); A1;,
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Reference of 2752-17-2, These common heterocyclic compound, 2752-17-2, name is 2,2′-Oxydiethanamine, 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.

o-Vanillin (1.82 g, 12 mmol) in EtOH (5 mL) was added dropwise to a 5 mL EtOH solution of3-oxapentane-1,5-diamine (0.52 g, 5 mmol). After the completion of addition, the solutionwas stirred for an additional 4 h at 78C. After cooling to room temperature, the precipitatewas filtered off. The product was dried in vacuo and obtained as a yellow crystalline solid.Yield: 1.59 g (68.0%). Anal. C20H24O5N2: Calcd C, 64.50; H, 6.50; N, 7.52%; found: C, 64.30; H,6.51; N, 7.51%. Selected IR data (KBr, nu/cm-1), 1629(nuC=N), 1256(nuC-O-C), 1047(nuOH). UV-vis(DMF): lambda = 271, 330 nm. Lambdam (DMF, 297 K): 1.7 S cm2 mol-1.

The synthetic route of 2752-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Xinkui; Mao, Shanshan; Shen, Kesheng; Wu, Huilu; Tang, Xia; Journal of Coordination Chemistry; vol. 70; 12; (2017); p. 2015 – 2028;,
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Adding a certain compound to certain chemical reactions, such as: 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 20781-20-8, SDS of cas: 20781-20-8

To a solution of 2-methyl-5-nitrobenzoic acid (1.0 g, 5.52 mmol) in methanol (10 mL) was added cone. H2S04 (0.5 mL) and the reaction mixture was heated at reflux for 16 h. Then the reaction mixture was concentrated and the residue was diluted with EtOAc. Then the mixture was washed with saturated aqueous NaHC03 solution, water and brine. The organic layer was separated, dried, filtered and concentrated to afford 1.0 g of methyl 2-methyl-5-nitrobenzoate which was used for the next step without further purification. A mixture of methyl 2-methyl-5-nitrobenzoate (1.0 g, 5.12 mmol) and l-ie/t-butoxy- N,N,N’,N’-tetramethylmethanediamine (2.23 g, 12.81 mmol) was heated at 1 15 C for 2 h. Then the reaction mixtuer was concentrated and purified by column chromatography to afford 600 mg of (E)-methyl 2-(2-(dimethylamino)vinyl)-5- nitrobenzoate. To a solution of (E)-methyl 2-(2-(dimethylamino)vinyl)-5- nitrobenzoate (600 mg, 2.40 mmol) in toluene (5 mL) was added (2,4- dimethoxyphenyl)methanamine (602 mg, 3.60 mmol) and the reaction mixture was heated at 120 C for 2 h. Then the reaction mixture was concentrated and the residue was triturated with EtOAc: Et20 (1 :9) and the solid precipitate was filtered and dried to afford 700 mg of the title product. 1H NMR (400 MHz, DMSO- 6): delta 9.32-9.31 (d, = 2.4 Hz, 1H), 8.41-8.38 (dd, = 2.4, 8.8 Hz, 1H), 7.62-7.60 (d, = 9.6 Hz, 1H), 7.48-7.46 (d, J = 7.2 Hz, 1H), 7.44-7.42 (d, J = 8.0 Hz, 1H), 6.52-6.49 (m, 3H), 5.15 (s, 2H), 3.86 (s, 3H), 3.82 (s, 3H).

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, (2,4-Dimethoxyphenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2014/167444; (2014); A1;,
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