Dimethylformamide → N-phenyl-2-chloroquinolinium chloride

참여 물질

반응 단계

The intermediate N-phenyl-2-chloroquinolinium chloride is prepared according to the literature method (Marson, TETRAHEDRON, 48, 3659 (1992)). Thus 1.06 g (5 mmoles) of N, N-diphenyl acetamide is heated with 1.69 g (11 mmoles) of phosphorous oxychloride and 0.44 g (6 mmoles) of DMF at 120° C. for 2 hours. The reaction mixture is cooled to room temperature and 15 mL of methylene chloride is added to dissolve the residue. To the solution is added 1.68 g (5 mmoles) of N,2-dimethylbenzothiazolium tosylate and 1.46 g (12 mmoles) of 4-dimethylaminopyridine, and the reaction is stirred overnight (Elderfield, supra). The crude product is first purified on a silica gel column eluting with 2:2:1 ethyl acetate/chloroform/methanol and then metathesized to the iodide salt and recrystallized from methanol to obtain the pure product.

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