3-AMINO-4-HYDROXY-5-METHOXYBENZOIC ACID HCL synthesis

Yield:15785-53-2 95.4%

Reaction Conditions:

with hydrogenchloride;palladium 10% on activated carbon;hydrogen in ethanol at 20;

Steps:

3. 3-Amino-4-hydroxy-5-methoxybenzoic acid (5-aminovanillic acid) hydrochloride 3

A mixture of 5-nitrovanillic acid (3 g, 139 mmol), palladium on carbon (10% Pd/C, 0.75 g, 25wt%) and 37% hydrochloric acid (3.2 mL, 141 mmol) in 200 mL ethanol was stirred at room temperature under H2 overnight. After filtration, the solvent was evaporated to dryness affording the product as a white powder. The yield was 2.94 g (95.4%), mp: 232°C (dec.) (215-257°C (dec.))³.

References:

Sun, Hong;Kanehashi, Shinji;Tsuchiya, Kousuke;Ogino, Kenji [Chemistry Letters,2016,vol. 45,# 4,p. 439 - 441] Location in patent:supporting information