Benzoic acid, 2-(methylamino)-3-nitro-, methyl ester → Benzoic acid, 3-amino-2-(methylamino)-, methyl ester

HRID 1698529Notes

Reaction equation

HRID 1698529 reaction equation
[CH3:1][NH:2][C:3]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>CO.[Pd]>[NH2:13][C:12]1[C:3]([NH:2][CH3:1])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 59635415Benzoic acid, 2-(methylamino)-3-nitro-, methyl ester

Product 1

HCID 59202087Benzoic acid, 3-amino-2-(methylamino)-, methyl esterYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 20.7 g (98 mmol) of methyl 2-methylamino-3-nitrobenzoate in 1200 mL of methanol was inerted with nitrogen. To this solution was added 5 g (2.3 mmol) 10% palladium on carbon (50% wet). The reaction was purged with hydrogen and stirred under balloon pressure hydrogen for 7 h. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to give 17.5 g (99%) of the title compound.

Workup

  1. customThe reaction was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-68ea76cf536241e090165d4f58efdb04
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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