Tert-butyl 2-nitro-4-(3-phenyl-1-propenyl)benzoate → Tert-butyl 2-amino-4-(3-phenylpropyl)benzoate

HRID 1673341Notes

Reaction equation

HRID 1673341 reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]([CH:17]=[CH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([O-])=O>[C].[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:16]=[C:15]([CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 67344218Tert-butyl 2-nitro-4-(3-phenyl-1-propenyl)benzoate

Product 1

HCID 67343055Tert-butyl 2-amino-4-(3-phenylpropyl)benzoateYield 109%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

62 mg of 5% palladium-carbon was added to 3 mL of ethyl acetate solution containing 0.31g of tert-butyl 2-nitro-4-(3-phenyl-1-propenyl)benzoate at room temperature and stirred under hydrogen atmosphere at the same temperature for 5 hours and 30 minutes. Insoluble were removed by filtration, and the solvent was evaporated under reduced pressure to obtain 0.31 g of tert-butyl 2-amino-4-(3-phenylpropyl)benzoate as yellow oil.

Workup

  1. customInsoluble were removed by filtration
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-893b0b0903d448debe129d403a377510
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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