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

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Reaction Steps

To a solution of tert-butyl 1,2,3,4-tetrahydroquinolin-3-yl-carbamate (28.3 g, 114 mmol), prepared as described in Example 1A, 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 saturated aqueous NaCl, dried Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc/hexanes (1:5 ratio) to give the title compound (10.6 g, 58% yield) as a white solid.

Provenance & Evidence