4-Hydroxy-3-nitrophenylacetic acid → (3-Amino-4-hydroxyphenyl)acetic acid

Participants

Reaction Steps

92.4 g of 4-hydroxy-3-nitrophenylacetic acid are suspended in a solution constituted by 785 ml of H2O and 21.2 g of NaHCO3. 5 g of a catalyst constituted by 5% Pd-on-carbon are suspended in the solution, which is then hydrogenated at ambient temperature for 4 hours, to obtain 4-hydroxy-3-aminophenylacetic acid. The catalyst is separated by filtration in a nitrogen environment, and the aqueous solution is used for the reaction with 4-fluorobenzoyl chloride, which is carried out in the following manner: the aqueous solution is cooled to 5° C. in a nitrogen environment, 460 ml of t-butylmethylether are added, and then 74 ml of 4-fluorobenzoyl chloride dissolved in 170 ml of t-butylmethylether are fed slowly.

Provenance & Evidence