3,4-dimethoxy-2-nitrobenzoic acid → 2-Amino-3,4-dimethoxybenzoic acid

HRID 354831Notes

Reaction equation

HRID 354831 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:14]([O-])=O)=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7].[H][H]>[OH-].[NH4+].[Pd]>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]=1[NH2:14]

Participants

5

Reactant 2

HCID 12522693,4-dimethoxy-2-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 117455912-Amino-3,4-dimethoxybenzoic acidYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14923Ammonium HydroxideSolvent

Procedure

A solution of 3,4-dimethoxy-2-nitro benzoic acid (1011 g., 4.45 moles) in 14 liters of 1.3 N ammonium hydroxide was reduced at 60 psi in presence of 60 grams of palladium on barium carbonate. Hydrogen uptake ceased after four hours. The reaction mixture was filtered through diatomaceous earth and acidified with glacial acetic acid (1.2 liters) to yield 685 grams (78%) of the anthranilic acid, M.P. 183°-184° C.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth

Sources & evidence

ORD record
ord-9f9306c19b6b4f69a7f9343fbd0387ff
Source dataset
uspto-grants-1983_03
Patent number
US04377581

Reaction notes

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