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

HRID 1458735Notes

Reaction equation

HRID 1458735 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) is hydrogenated at 55 psi in the presence of 10% palladium on carbon (5.8 g) for 2.5 hours. The reaction mixture is filtered through SUPERCELL™, the filter cake is rinsed with ethanol, and then the filtrate is poured into ice water (3.5 L). A precipitate forms which is 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 is filtered through SUPERCELL™
  2. washthe filter cake is rinsed with ethanol
  3. additionthe filtrate is poured into ice water (3.5 L)
  4. filtrationA precipitate forms which is collected by filtration
  5. washwashed with water
  6. customdried in an oven at 60° C.

Sources & evidence

ORD record
ord-2c34d510a29d4c689a245ddceeadeb1e
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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