Sodium Hydroxide → (2-Chloro-6-methoxyquinolin-4-yl)acetonitrile

Participants

Reaction Steps

[2-(2-Chloro-6-methoxyquinolin-4-yl)ethenyl]dimethylamine (28.3 g, 0.11 mol) and hydroxylamine-O-sulfonic acid (40.2 g, 0.36 mol) were suspended in water (1.2 L), and the mixture was stirred at room temperature for 70 hours. The reaction mixture was neutralized with an aqueous solution of sodium hydroxide, and the organic materials were extracted with a mixed solvent of 5% methanol/ethyl acetate. The extract was washed with saturated brine and water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was recrystallized from ethyl acetate to obtain the title compound (19.9 g, 79%).

Provenance & Evidence