Chloroform → N-(1,2,3,4-tetrahydroquinolin-3-yl)acetamide
Reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:3])[CH3:2].C(Cl)(Cl)Cl>C(O)(=O)C>[C:1]([NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH2:6]1)(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Borane-pyridine complex (320 mg, 3.5 mmol) was added to a solution of 3-acetamidoquinoline (320 mg, 1.7 mmol) in acetic acid (20 ml) and the mixture was stirred at room temperature for 18 h. Chloroform (150 ml) was added and the mixture was washed with 2N sodium hydroxide solution, water and brine. The organic phase was dried and reduced. Chromatography (80% EtOAc/20% 60-80 pet. ether) afforded 3-acetamido-1,2,3,4-tetrahydroquinoline (180 mg, 55%) as a pale yellow solid.