2,3-Dimethoxy-6-nitrobenzoic acid → 6-Amino-2,3-dimethoxybenzoic acid

HRID 980877Notes

Reaction equation

HRID 980877 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([N+:14]([O-])=O)[C:4]=1[C:5]([OH:7])=[O:6]>CCO.[Pd]>[NH2:14][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 127623792,3-Dimethoxy-6-nitrobenzoic acid

Product 1

HCID 117455906-Amino-2,3-dimethoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A slurry of 2,3-dimethoxy-6-nitrobenzoic acid (5 g, 22 mM) in EtOH (200 ml) was treated with Pd/C (5%, 0.5 g) and the mixture hydrogenated on a Parr apparatus at 45 psi for 1 hour. The reaction mixture was filtered and the solvent removed from the filtrate. An off-white semi-solid residue was isolated. Crystallization from isopropanol afforded the amine, 3.8 g (86.7%), mp 71°-72° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed from the filtrate
  3. customAn off-white semi-solid residue was isolated
  4. customCrystallization from isopropanol

Sources & evidence

ORD record
ord-1df775315dd348a0936fe08f874ac167
Source dataset
uspto-grants-1987_01
Patent number
US04639518

Reaction notes

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