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Add 50 g of 1,3-dichloro-6-bromoisoquinoline to 500 mL of glacial acetic acid, and then add 14 g of red phosphorus.Hydrochloric acid 100 mL, then the system was heated to reflux, the reaction was about 5 h, and TLC confirmed the reaction was complete.After-treatment: cool to room temperature, suction filtration, add 500 mL of water to the filter cake.The mixture was adjusted to pH = 8 with 15percent aqueous ammonia, filtered, and the filtrate was extracted with ethyl acetate.The acetic acid phase is dried, added with water and alkali, extracted with ethyl acetate, and combined with all organic phases.Wash once with saturated brine, dry over anhydrous sodium sulfate, spin dry,The column was passed through 200-300 mesh silica gel, petroleum ether: ethyl acetate = 50:1 to 20:1.The product 3-chloro-6-bromoisoquinoline 30 g was obtained in a yield of 68.4percent.
50%
With HI In acetic acid; ethyl acetate
Example 80C 6-Bromo-3-chloro-isoquinoline A mixture of Example 80B (1.8 g, 6.5 mmol), P (0.48 g, 15.5 mmol) and HI (3 ml, 48percent) in acetic acid (20 ml) was refluxed for 8 hours, filtrated under hot condition and concentrated under vacumm. The residue was basified by adding sodium hydroxide solution, treated with ethyl acetate (200 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30percent ethyl acetate/hexane to provide the title compound (0.81 g, 50percent). MS (DCI/NH3) m/e 244 (M+H)+.
50%
Stage #1: With phosphorus; hydrogen iodide In water; acetic acid for 8 h; Heating / reflux Stage #2: With sodium hydroxide In water
Example 80C 6-Bromo-3-chloro-isoquinoline A mixture of Example 80B (1.8 g, 6.5 mmol), P (0.48 g, 15.5 mmol) and HI (3 ml, 48percent) in acetic acid (20 ml) was refluxed for 8 hours, filtrated under hot condition and concentrated under vacumm. The residue was basified by adding sodium hydroxide solution, treated with ethyl acetate (200 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30percent ethyl acetate/hexane to provide the title compound (0.81 g, 50percent). MS (DCI/NH3) m/e 244 (M+H)+.
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