Methyl 4-(2-nitrophenyl)butanoate → Methyl 4-(2-aminophenyl)butanoate

HRID 2189032Notes

Reaction equation

HRID 2189032 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13]

Participants

4

Reactant 1

HCID 11401810Methyl 4-(2-nitrophenyl)butanoate

Product 1

HCID 237256Methyl 4-(2-aminophenyl)butanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

Initially charge 715 mg (3.2 mmol) of 4-(2-nitrophenyl)butanoic acid methyl ester in 1.5 ml of ethanol, add 34 mg of palladium on activated carbon (10%) under argon and stir under a hydrogen atmosphere (standard pressure) at RT overnight. In order to complete the reaction, add more palladium on activated carbon and stir at RT under a hydrogen atmosphere for a further 24 h. Filter the catalyst off and concentrate the solution under reduced pressure. 229 mg (37.1% of theory) of the target product are obtained.

Workup

  1. customthe reaction
  2. stirringstir at RT under a hydrogen atmosphere for a further 24 h
  3. filtrationFilter the catalyst off and
  4. concentrationconcentrate the solution under reduced pressure
  5. custom229 mg (37.1% of theory) of the target product are obtained

Sources & evidence

ORD record
ord-36540c304c484d378e444bdae4439511
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

Loading…