Ethyl 4-amino-2-methoxy-5-nitrobenzoate → Ethyl 4,5-diamino-2-methoxybenzoate

HRID 1465806Notes

Reaction equation

HRID 1465806 reaction equation
[NH2:1][C:2]1[C:12]([N+:13]([O-])=O)=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([O:16][CH3:17])[CH:3]=1>CO.[Pd]>[NH2:1][C:2]1[C:12]([NH2:13])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

4

Reactant 1

HCID 67231122Ethyl 4-amino-2-methoxy-5-nitrobenzoate

Product 1

HCID 67230016Ethyl 4,5-diamino-2-methoxybenzoateYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-amino-2-methoxy-5-nitrobenzoate (248 mg, 1.03 mmol) in methanol (20 ml) was added 5% palladium on activated carbon (85 mg) and the mixture stirred vigorously at room temperature under a hydrogen atmosphere for 18 h. The reaction mixture was then filtered through celite, the catalyst/residue washed with methanol and the combined filtrate and washings concentrated to give crude ethyl 4,5-diamino-2-methoxybenzoate (220 mg, 100%) as a dark-brown material, which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. washthe catalyst/residue washed with methanol
  3. concentrationthe combined filtrate and washings concentrated

Sources & evidence

ORD record
ord-251e3a655ecf431a973d710fcb8cdfcd
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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