Chlorosuccinimide → 2-Chloro-3-(quinolin-6-yl)propanal

Reaction equation

N1CCC[C@H]1C(O)=O.[N:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH:21]=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[Cl:23]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:23][CH:20]([CH2:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:9]=[CH:10][CH:11]=[CH:12]2)[CH:21]=[O:22]

Participants

Procedure

L-Proline (410 mg, 3.5 mmol) was added to a solution of 3-quinolin-6-ylpropanal (3.27 g, 17.6 mmol) in chloroform (39 mL) at 0° C. followed by addition of N-chlorosuccinimide (2.48 g, 18.5 mmol) and the reaction mixture was slowly warmed to ambient temperature and stirred for 1 h, monitoring by LCMS. The solvent was concentrated under reduced pressure and the residue was purified on a silica gel column with ethyl acetate in hexane (0-50%) to give the desired product. (95%) LCMS: (M+H+H2O)=237.9/239.9.