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

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of p-toluenesulfonyl chloride (6.19 g, 0.0325 mol) in dichloroethane (75 mL) was added 2,6 dimethylquinaldine N-oxide (2) (5 g, 0.0289 mol) under N2. The reaction mixture was then heated to 100° C. for 24 hours, cooled, concentrated and extracted with 10% K2CO3 and ethyl acetate. The organic layer was dried with MgSO4, concentrated and purified on a small silica flash column (2:1 dichloromethane:hexanes). The resulting yellow solid was then recrystallized in hexanes to afford 3.31 g (60%) of a white solid. H1 NMR (CDCl3): δ 2.50 (s, 3H) 4.80 (s, 2H), 7.40-7.50 (m, 2H), 7.58-7.61 (d, 1H), 8.02-8.99 (m, 1H), 8.11-8.14 (d, 1H).

Provenance & Evidence