反应详情

To a stirred suspension of dimethyl-7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (2.00 g, 6.80 mM) and 1-naphthylhydrazine hydrochloride (9.26 g, 47.6 mM) in ethanol (72 mL) was added triethylamine (7.60 mL) to give a brown solution. After refluxing for 4 days, the solution was cooled to room temperature and diluted with ethyl acetate (0.35 L) to give a tan suspension. This suspension was filtered to remove the solids which were discarded. The filtrate was then poured into ethyl acetate (500 mL) which was washed with hydrochloric acid (3×500 mL, 1N). The washed solution was diluted with ether (250 mL) to give a tan suspension. The solids were collected to give the 1-naphthylhydrazine salt of the title compound as a tan powder (2.09 g). This material was refluxed in glacial acetic acid (50 mL) for 2 hours, cooled to room temperature and filtered. The collected solids were washed with glacial acetic acid and ether to give the title compound (1.44 g, 54%) as a tan powder, mp 368° C. (decomp.); MS(CI): 390 (M+H).

1. customto give a brown solution
2. temperatureAfter refluxing for 4 days
3. customto give a tan suspension
4. filtrationThis suspension was filtered
5. customto remove the solids which
6. additionThe filtrate was then poured into ethyl acetate (500 mL) which
7. washwas washed with hydrochloric acid (3×500 mL, 1N)
8. additionThe washed solution was diluted with ether (250 mL)
9. customto give a tan suspension
10. customThe solids were collected