N-[5-(3-cyanophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide → N-{5-[3-(aminomethyl)phenyl]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH2:20][CH:19]([NH:24][S:25]([CH:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])[CH2:18]3)[CH:12]=[CH:13][CH:14]=1)#[N:8]>O1CCCC1>[NH2:8][CH2:7][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[CH2:20][CH:19]([NH:24][S:25]([CH:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])[CH2:18]3)[CH:12]=[CH:13][CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 1.0M solution of lithium aluminium hydride in tetrahydrofuran (8 ml) was cooled to 0° C. in an ice/methanol bath with stirring under argon. The solution was then treated dropwise with a solution of N-[5-(3-cyanophenyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (0.67 g, 1.97 mmol) in dry tetrahydrofuran (20 ml) over 15 mins. The cooling bath was removed and the whole mix stirred at reflux for 2 h. The reaction mix was allowed to cool to room temperature and quenched with water (0.8 ml), 10% NaOH (0.8 ml), and water again (1.2 ml). The reaction mix was dried over sodium sulphate, filtered and the filtrate evaporated under reduced pressure to give the title compound as a yellow oil (0.67 g, 100%).