1-(2-Nitrophenyl)cycloheptene → 2-Cycloheptylphenylamine
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1)([O-])=O>[Pd].CO>[CH:10]1([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of the 1-(2-nitrophenyl)cycloheptene (1.00 g, 4.61 mmol) produced in Example (44a), 10% palladium on carbon (300 mg, wet) and methanol (130 mL) was stirred for 21 hours at atmospheric pressure and room temperature under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/heptane) to give 539 mg of the title compound as a light orange oil.