Benzoic acid, 3,4,5-trimethoxy-2-nitro-, methyl ester → Methyl 3,4,5-trimethoxyanthranilate

HRID 1156015Notes

Reaction equation

HRID 1156015 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[C:5]=1[N+:16]([O-])=O>CO.[H][H].[Pd]>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[C:5]=1[NH2:16]

Participants

5

Reactant 1

HCID 78765Benzoic acid, 3,4,5-trimethoxy-2-nitro-, methyl ester

Product 1

HCID 78735Methyl 3,4,5-trimethoxyanthranilateYield 92.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundCatalystHCID 887MethanolSolvent

Procedure

The latter nitro derivative (17.0 g) in 500 ml of methanol was reduced at room temperature and pressure with hydrogen using 4 g of 10% palladium on carbon as catalyst for 6 hr and filtered. The solvent was removed to give 14 g of 2-amino-3,4,5-trimethoxybenzoic acid methyl ester as an oil.

Workup

  1. customwas reduced at room temperature
  2. filtrationfiltered
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-c33b5f4bb4104c008337019d17fca287
Source dataset
uspto-grants-1982_06
Patent number
US04333937

Reaction notes

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