Benzoic acid, 4-hydroxy-3-nitro-, methyl ester → Methyl 3-amino-4-hydroxybenzoate

HRID 1422061Notes

Reaction equation

HRID 1422061 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-])=O>C(OCC)(=O)C.[C].[Pd]>[NH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

Product 1

HCID 10815Methyl 3-amino-4-hydroxybenzoateYield 97%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the objective compound (11.4 g, 57.8 mmol) of Step (1) in ethyl acetate (300 mL) was added under nitrogen atmosphere 10% palladium carbon (1.80 g) and the mixture was stirred at room temperature for 18 hours under hydrogen atmosphere. The catalyst was filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The obtained solid was washed with ether-hexane (1:1) and dried in vacuo to give methyl 3-amino-4-hydroxybenzoate as a pale-brown solid (9.34 g, 97%).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washThe obtained solid was washed with ether-hexane (1:1)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-69a8aef7c3dc4ee89058b06cc5c70c75
Source dataset
uspto-grants-2000_06
Patent number
US06080738

Reaction notes

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