4-Methoxy-2-nitrobenzoic acid → 2-Amino-4-methoxybenzoic acid

HRID 1456019Notes

Reaction equation

HRID 1456019 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O>CN(C=O)C.[Pd]>[CH3:14][O:13][C:11]1[CH:12]=[C:4]([NH2:1])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 2886574-Methoxy-2-nitrobenzoic acid

Product 1

HCID 3510102-Amino-4-methoxybenzoic acidYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

2-Nitro-4-methoxybenzoic acid (43.4 g, 0.22 mol) in DMF (250 ml) was hydrogenated at 55 psi in the presence of 10% palladium on carbon (5.8 g) for 2.5 hours. The reaction mixture was filtered through SUPERCELL®, the filter cake was rinsed with ethanol and then the filtrate was poured into ice/water (3.5 L). A precipitate formed which was collected by filtration, washed with water and dried in an oven at 60° C. to afford 30.7 g (84%) of 4-methoxyanthranilic acid, m.p. 176°-178° C. (dec.).

Workup

  1. filtrationThe reaction mixture was filtered through SUPERCELL®
  2. washthe filter cake was rinsed with ethanol
  3. additionthe filtrate was poured into ice/water (3.5 L)
  4. customA precipitate formed which
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in an oven at 60° C.

Sources & evidence

ORD record
ord-097dbd949baf4c578eb5e21b5a4e5037
Source dataset
uspto-grants-1998_12
Patent number
US05843956

Reaction notes

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