Methyl 3-(methylamino)-4-nitrobenzoate → Methyl 4-amino-3-(methylamino)benzoate

HRID 417323Notes

Reaction equation

HRID 417323 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:6]([O:8][CH3:9])=[O:7]>C(OCC)(=O)C.[Pd]>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:12]([NH2:13])=[C:3]([NH:2][CH3:1])[CH:4]=1

Participants

4

Reactant 1

HCID 15892779Methyl 3-(methylamino)-4-nitrobenzoate

Product 1

HCID 57835341Methyl 4-amino-3-(methylamino)benzoateYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl 3-(methylamino)-4-nitrobenzoate (Bionet) (0.5 g, 2.4 mmol) and Pd/C (Aldrich, 10%, 0.1 g) in ethyl acetate (7 mL) was vigorously shaken in a Parr under atmosphere of H2 (50 psi) for 0.5 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to give 4-amino-3-methylamino-benzoic acid methyl ester as a dark brown foam (0.4 g, 93%).

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1129d4435c914483a9ae61e22fa7d89f
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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