HCID 22663345, compound → Benzoic acid, 2,3-diamino-4-methoxy-, methyl ester (9CI)

HRID 380413Notes

Reaction equation

HRID 380413 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([O:15][CH3:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]([O:15][CH3:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 22663345HCID 22663345, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22663264Benzoic acid, 2,3-diamino-4-methoxy-, methyl ester (9CI)Yield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl 2-amino-4-methoxy-3-nitrobenzoate (1.84 g, Reference Example 9) in ethanol (100 ml) was treated with 10% palladium on carbon (0.2 g). The resulting suspension was stirred under 3 atmospheres of hydrogen for 3 hours. The catalyst was then removed by filtration and the filtrate evaporated to give the title compound (1.6 g) as a black solid which was used without further purification. M+196.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-e2275780ed254174ba06411740f938fd
Source dataset
uspto-grants-2001_10
Patent number
US06303600B1

Reaction notes

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