Uses
Methyl 3-Amino-4-carboxybenzoate is an intermediate used to prepare (N-methylpiperazinyl)-contg. derivatives of quinazolinone as fungal efflux pump inhibitors.
Synthesis
General procedure for the synthesis of 2-amino-4-methoxycarbonylbenzoic acid from methyl 3-nitro-4-carboxybenzoate: preparation Example 12 Step 1. A suspension of 2-amino-4-(methoxycarbonyl)benzoic acid 12BA (4-methoxycarbonyl)-2-nitrobenzoic acid (12A) (10.0 g, 44.4 mmol) with 5% Pd/C (4.0 g) was reacted in a 1. 1 MeOH/H2O (50 mL) were mixed and placed under hydrogenation conditions (H2, 50 psi) for 16 hrs of reaction. Upon completion of the reaction, the mixture was filtered through a Celite pad, washed with MeOH, and the filtrate was concentrated to give the product 12B (6.51 g, yield = 75%). Mass spectral analysis showed MS (M+H) = 196.
References
[1] Patent: WO2012/51036, 2012, A1. Location in patent: Page/Page column 79
[2] Patent: US5541178, 1996, A
[3] Monatshefte fuer Chemie, 1907, vol. 28, p. 822
