2-(2-Nitrophenyl)pyridine → 2-(2-Pyridinyl)benzenamine

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O.[BH4-].[Na+]>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13]

Participants

Procedure

Next, 0.96 g (4.8 mmols) of the ortho-(2-pyridyl)nitrobenzene, 0.072 g (0.48 mmol) of copper sulfate and 0.91 g (24.0 mmols) of sodium borohydride were suspended in 30 ml of ethyl alcohol and allowed to react at room temperature. After 5 hours from the start of the reaction, the reaction mixture was filtered through celite, 50 ml of ether was added to the filtrate, the organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The liquid thus obtained was purified by column chromatography and concentrated to give 0.38 g (2.26 mmoles, 47%) of ortho-(2-pyridyl)aniline as a brown liquid.