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

Participants

Reaction Conditions

Reaction Steps

6-Methoxyquinaldine N-Oxide (6.94 g, 36.71 mmol) was added to a stirring solution of p-toluenesulfonylchloride (7.0 g, 36.84 mmol) in dichloroethane (100 mL). The reaction was heated to 100° C. overnight, partitioned between 10% K2CO3 /ethyl acetate, dried over MgSO4, and evaporated under reduced pressure. The crude solid was purified by HPLC to afford 2.6 g (37%) of chloride.

Provenance & Evidence