3,4-Dimethoxy-2-nitrobenzoic acid → 2-Amino-3,4-dimethoxybenzoic acid
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
Product 1
Reagents, catalysts & solvents 2
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
- 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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