4-Hydroxy-3-nitrobenzoic acid → 3-Amino-4-hydroxybenzoic acid

HRID 626216Notes

Reaction equation

HRID 626216 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-])=O>CO.[Pd]>[NH2:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[OH:1])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 120334-Hydroxy-3-nitrobenzoic acid

Product 1

HCID 650833-Amino-4-hydroxybenzoic acidYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-hydroxy-3-nitrobenzoic acid (10 g, 1.0 eq) and 2 g Pd/C in 100 mL MeOH was stirred at rt under H2 (1 atm) overnight, and then filtered. The filtrate was concentrated under reduced pressure to afford the desired product (8.0 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ 10.00 (brs, 1H), 7.19 (s, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.67 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-13ef310e9cfe498f968ab95134f84271
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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