Water → tert-Butyl 6-chloro-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Participants

Reaction Steps

To a solution of 1A (28.3 g, 114 mmol) in acetonitrile (240 mL) at RT was added dropwise a solution of N-chlorosuccinimide (15.22 g, 114 mmol) in acetonitrile (240 mL). After addition, the reaction mixture was stirred for 6 h, then water (500 mL) added. The mixture was extracted with EtOAc (2×500 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc/hexane 1:5 to give the title compound (10.6 g, 58% yield) as a white solid.

Provenance & Evidence