Chlorosuccinimide → 6-Chloro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

Based on R. Nagata et al., J. Med. Chem., 1994, 37, 3956-3968, 1,2,3,4-tetrahydroquinoline (1.33 g, 10 mmol) was dissolved in DMF (15 mL) under N2 and cooled to 0° C. N-Chlorosuccinimide (1.35 g, 10 mmol) was dissolved in DMF (10 mL) under N2 and was added to the tetrahydroquinoline solution dropwise, via pressure equalizing dropping funnel, over 45 min. The reaction was stirred at 0° C. for 3 h, then quenched by pouring it into water (100 mL). This mixture was extracted with a 5:1 mixture of EtOAc:toluene, then two times with EtOAc. All of the organic extracts were washed with brine, combined, dried over Na2SO4, filtered, and concentrated, then eluted through a 17×2.5 cm column of silica gel (5%, 10% and 15% EtOAc/Hexane step gradient) giving 6-chloro-1,2,3,4-tetrahydroquinoline as a green oil.

Provenance & Evidence