1,2-Dichloroethane → Tert-butyl 6-(2-benzoylhydrazino)-5-chloronicotinate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-chloro-6-hydrazinonicotinate hydrochloride salt (3.0 g, 9.5 mmol) in N,N-dimethylformamide (20 mL) were added benzoic acid (1.62 g, 13.3 mmol), EDC (3.63 g, 19.0 mmol), HOAT (1.29 g, 9.48 mmol) and triethylamine (6.6 mL, 48.4 mmol). The reaction mixture was stirred at 60° C. After 1 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3×). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated: LC-MS [M+1]=348.1.

Provenance & Evidence