Tetrahydrofuran → N-[1-[(2Z)-2-amino-2-hydroxyiminoethyl]-2-oxo-3,4-dihydroquinolin-3-yl]-5-chloro-1H-indole-2-carboxamide

Participants

Reaction Steps

A solution hydroxylamine hydrochloride (147 mg, 2.11 mmol) in MeOH (4 mL) was added to a solution of sodium methoxide in methanol (0.5 M, 4.2 mL, 2.1 mmol) that had been further diluted with methanol (4 mL). After stirring for 10 minutes, THF (4 mL) was added followed by portionwise addition of 5-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide (Method 11, 400 mg, 1.06 mmol). The reaction mixture was stirred at ambient temperature for 18 h, partitioned between EtOAc (80 mL) and diluted brine (80 mL), filtered and the layers of the filtrate separated. The organic phase was dried (Na2SO4) and the volatiles removed under reduced pressure to give the title material (191 mg, 44%) as a yellow solid.

Provenance & Evidence