Ammonium Chloride → HCID 68521214, compound
Reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH:10]=[N:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1.[In].[NH4+].[Cl-]>CCO>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][NH:9][CH2:8][CH2:7]3)[CH2:3][CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-cyclopropylisoquinoline (0.500 g, 0.003 mol) in EtOH (15 mL) was added indium powder (3 g) and saturated aqueous NH4Cl (5 mL). The reaction mixture was heated at reflux for 36 h while stirring. After completion, the reaction mixture was filtered through Celite® (diatomaceous earth) and the filtrate concentrated at reduced pressure to afford crude 6-cyclopropyl-1,2,3,4-tetrahydro-isoquinoline. Purification was done by silica gel column chromatography eluting with MeOH in CH2Cl2 (0-10%) to afford pure 6-cyclopropyl-1,2,3,4-tetrahydro-isoquinoline (0.300 g, 58%) as a white solid.