1-(4-Nitrophenyl)cyclopropanecarboxylic acid → 1-(4-Aminophenyl)cyclopropanecarboxylic acid

HRID 714858Notes

Reaction equation

HRID 714858 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 200261851-(4-Nitrophenyl)cyclopropanecarboxylic acid

Product 1

HCID 666623781-(4-Aminophenyl)cyclopropanecarboxylic acidYield 60.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(4-nitrophenyl)cyclopropanecarboxylic acid (500 mg) obtained in Step B of Example 145 in ethanol (10 mL) was added palladium-activated carbon ethylene diamine complex (Pd 8.5 to 11.5%) (100 mg), and the mixture was stirred overnight at room temperature under hydrogen atmosphere (at normal pressures). The palladium carbon was removed by filtration through Celite, and the solvent was evaporated under reduced pressure to give the title compound (260 mg).

Workup

  1. customThe palladium carbon was removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-92bc863eab8d40349292867908d82bf6
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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