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

HRID 375869Notes

Reaction equation

HRID 375869 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.[H][H]>[Pd].[OH-].[NH4+]>[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

5

Reactant 2

HCID 2886574-Methoxy-2-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 3510102-Amino-4-methoxybenzoic acidYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of 2-nitro-4-methoxybenzoic acid (21.9 g, 0.111 mol), 2N ammonium hydroxide (250 ml) and 5% palladium on strontium carbonate (2.5 g) was shaken under 45 psi of hydrogen pressure for 3-4 hours. The reaction mixture was filtered, and the filtrate was acidified with acetic acid. A solid formed which was collected by filtration, washed with water and dried to afford 16 g of 4-methoxyanthranilic acid, m.p. 194°-195° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customA solid formed which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-832ff33842844a1293640503aeb97e66
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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