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

HRID 1498889

Reaction equation

HRID 1498889 reaction equation
[CH3:1][NH:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[N+:14]([O-])=O>CO.[Pd]>[NH2:14][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:3]=1[NH:2][CH3:1])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 1

HCID 12493881Ethyl 4-(methylamino)-3-nitrobenzoate

Product 1

HCID 2824047Ethyl 3-amino-4-(methylamino)benzoateYield 82.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 4-methylamino-3-nitrobenzoate (6.80 g, 30.3 mmol) prepared in the Step 1-1-2 was dissolved in methanol (200 ml), and palladium 5% on carbon (1.10 g) was added to the solution. The mixture was stirred under a hydrogen flow at a room temperature overnight. The mixture was filtered, and the filtrate was concentrated to give the title compound (4.85 g, 82%) as a light-brown powder.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e5d48e67e449412cbe7fe268969a58ce
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Linked notes

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