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

HRID 1703393Notes

Reaction equation

HRID 1703393 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-9a816884d15947a5ad1e36796f4a8925
Source dataset
uspto-grants-1982_09
Patent number
US04351940

Reaction notes

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