3-Methoxy-2-nitrobenzoic acid → 2-Amino-3-methoxybenzoic acid

HRID 973558Notes

Reaction equation

HRID 973558 reaction equation
[N+:1]([C:4]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O>C(O)C.[Pd]>[CH3:14][O:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]=1[NH2:1]

Participants

4

Reactant 1

HCID 786323-Methoxy-2-nitrobenzoic acid

Product 1

HCID 2557202-Amino-3-methoxybenzoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Nitro-3-methoxybenzoic acid (10 g, 0.051 mol) was suspended in ethanol with palladium/charcoal 10% (1 g). The mixture was placed under hydrogen (50 psi) and shaken on a Parr until theoretical uptake had been achieved. The suspension was then flushed with nitrogen, the charcoal filtered off, and the filtrate evaporated in vacuo to give 3-methoxyanthranilic acid (7.76 q, 91%) m.p. 172°-175°.

Workup

  1. customThe suspension was then flushed with nitrogen
  2. filtrationthe charcoal filtered off
  3. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-3c8628796c554844bcf335a4b4777e12
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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