反应详情

A mixture of 1.399 g of 1-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (5 mmol) and 2.86 g of phenol was heated at 145° C. to 150° C. for 24 h. After cooling to ambient temperature the mixture was suspended in 50 ml of aqueous 2N NaOH and the mixture was extracted with 4×25 ml of ethyl acetate. The combined organic phases were washed with 3×25 ml of aqueous 2N NaOH, 50 ml of brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with hexanes:ethyl:acetate (9:1) and (95:5). 0.650 g of the title compound were obtained; 1H NMR (CDCl3): δ=11.52 (s, 1H), 8.32 to 8.39 (m, 2H), 7.72 to 7.86 (m, 2H), 7.13 to 7.42 (m, 5H), 4.31 (t, 2H), 1.69 (m, 2H), 1.37 (m, 2H), 0.93 (t, 3H).

1. temperaturewas heated at 145° C. to 150° C. for 24 h
2. extractionthe mixture was extracted with 4×25 ml of ethyl acetate
3. washThe combined organic phases were washed with 3×25 ml of aqueous 2N NaOH, 50 ml of brine
4. dry with materialdried over MgSO4
5. customevaporated in vacuo
6. customThe residue was purified by flash column chromatography on silica gel eluting with hexanes:ethyl:acetate (9:1) and (95:5)