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

HRID 1665221

Reaction equation

HRID 1665221 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]>O1CCCC1.[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 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 2-(methylamino)-3-nitrobenzoate (2.10 g, 10.0 mmol) in tetrahydrofuran (40 mL) was added palladium on carbon (210 mg), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen for 2 hr at room temperature. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound (1.80 g, 10.0 mmol, 100%) as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-12a9ff79db85438388d53b49bc1aff21
Source dataset
uspto-grants-2011_10
Patent number
US08039500B2

Linked notes

Loading…