Methyl 4-amino-3-methoxybenzoate synthesis
- Product Name:Methyl 4-amino-3-methoxybenzoate
- CAS Number:41608-64-4
- Molecular formula:C9H11NO3
- Molecular Weight:181.19
5081-37-8
41608-64-4
The general procedure for the synthesis of methyl 4-amino-3-methoxybenzoate from methyl 3-methoxy-4-nitrobenzoate was as follows: methyl 3-methoxybenzoate (83.0 g, 500 mmol) was added drop-wise to a mixture of acids consisting of HNO3 (65% by weight, 40 ml) and H2SO4 (70% by weight, 200 ml) at 0 °C. The reaction mixture was stirred overnight and poured into ice water. The mixture was filtered and the solid filter cake was washed with water (3 x 300 ml) to give 84.4 g of methyl 4-nitro-3-methoxybenzoate as a yellow solid in 80% yield. Next, an ethanol (1500 ml) solution of methyl 4-nitro-3-methoxybenzoate (84.4 g, 400 mmol) was stirred with Pd/C (10% Pd, 5.35 g) catalyst for 5 h under H2 atmosphere. After completion of the reaction, the catalyst was removed by Celite? filtration. The solvent was evaporated in vacuum to give an off-white solid. Finally, the off-white solid was recrystallized from methanol to give methyl 4-amino-3-methoxybenzoate (70.95 g, 392 mmol) in 98% yield.
Yield:41608-64-4 100%
Reaction Conditions:
Stage #1:methanol;3-methoxy-4-aminobenzoic acid;sulfuric acid at 70; for 24 h;
Stage #2: with sodium hydroxide in water; pH=8
Steps:
BA-20
A solution of 4-amino-3-methoxybenzoic acid (1.5 g, 8.97 mmole) in 15 ml methanol and 4.8 ml sulfuric acid 95-98% was heated at 70° C. for 24 hrs. Upon completion, the mixture was concentrated down and basified with 2N NaOH solution to pH=8. A solid precipitated out. The suspension was filtered off, solid was washed with water, dried to afford 1.62 g tan solid (56), 100% yield. 1H-NMR (400 MHz, DMSO)
References:
DECODE GENETICS EHF US2009/130076, 2009, A1 Location in patent:Page/Page column 31; 32
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