Reference of 27492-84-8, These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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.
(1) Methyl 2-methoxy-4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carboxamido]benzoate [Show Image] A suspension of 6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenecarboxylie acid (0.100 g) in anhydrous benzene (3 ml) was added with thionyl chloride (1 ml), and the mixture was refluxed by heating for 3 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in anhydrous benzene (2 ml) and pyridine (5 ml), the solution was added with methyl 2-methoxy-4-aminobenzoate (0.087 g) and 4-dimethylaminopyridine (one pellet), and the mixture was stirred overnight at room temperature. The reaction mixture was added with 2 N aqueous hydrochloric acid and thereby made acidic, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, 10percent aqueous sodium carbonate, and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane = 1:5) to obtain the title compound (0.145 g, yield: 85percent). 1H-NMR (400MHz, CDCl3): delta 1.17 (3H, s), 1.51 (2H, td, J=12.9, 5.1Hz), 1.71 (2H, dt, J=12.9, 3.9Hz), 1.78-1.89 (2H, m), 1.99-2.15 (2H, m), 2.82 (2H, dt, J=17.1, 8.6Hz), 2.96 (2H, ddd, J=17.1, 7.8, 3.0Hz), 3.87 (3H, s), 3.93 (3H, s), 6.97 (1H, dd, J=8.4, 1.8Hz), 7.38 (2H, s), 7.82 (1H, d, J=1.8Hz), 7.85 (1H, d, J=8.4Hz), 8.05 (1H, br-s)
Statistics shows that Methyl 4-amino-2-methoxybenzoate is playing an increasingly important role. we look forward to future research findings about 27492-84-8.
Reference:
Patent; Research Foundation Itsuu Laboratory; EP2189443; (2010); A1;,
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