4-Toluenesulfonyl chloride → 2-(Chloromethyl)-6-nitroquinoline

Participants

Reaction Conditions

Reaction Steps

2-Methyl-6-nitroquinoline N-oxide (13.0 g, 63.72 mmol) was added to a stirring solution of p-toluenesulfonyl chloride (13.5 g, 70.81 mmol) in dichloroethane (200 mL). The reaction was stirred overnight at 100° C. and then stirred at room temperature for 2 days. To the reaction mixture was added ethyl acetate. A solid precipitated and was filtered and recrystallized from acetone/water to afford 7.91 g (56%) of pure product.

Provenance & Evidence