反应详情

A mixture of 432 mg of 1-bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (1 mmol), 63 mg of red phosphorous (2 mmol), 0.4 ml of aqueous 57 wt % HI (3 mmol), and 1 ml of glacial acetic acid was refluxed with stirring for 30 min. Then the reaction mixture was diluted with 25 ml of ethyl acetate, filtered by suction through a pad of celite, washed with a solution of 0.2 g of NaHSO3 in 5 ml of water, and washed twice with 5 ml of concentrated aqueous sodium bicarbonate solution. The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with hexanes:ethyl acetate (85:15). 123 mg of the title compound were obtained; 1H NMR (CDCl3): δ=11.85 (s, 1H), 8.60 (s, 1H), 8.23 (d, 1H), 7.38 to 7.63 (m, 7H), 4.49 (t, 2H), 1.87 (m, 2H), 1.47 (m, 2H), 0.98 (t, 3H).

1. temperaturewas refluxed
2. filtrationfiltered by suction through a pad of celite
3. washwashed with a solution of 0.2 g of NaHSO3 in 5 ml of water
4. washwashed twice with 5 ml of concentrated aqueous sodium bicarbonate solution
5. dry with materialThe organic phase was dried over MgSO4
6. customevaporated in vacuo
7. customThe residue was purified by flash column chromatography on silica gel eluting with hexanes:ethyl acetate (85:15)