Phosphorus oxychloride → 1-Chloro-6-methyl-5-nitroisoquinoline

Participants

Reaction Steps

6-Methyl-5-nitroquinoline (46.5 g, 0.228 mol) obtained in Step (3) was dissolved in 1,2-dichloroethane (1.8 L), added with POCl3 (107 mL, 1.14 mol) at room temperature, and refluxed for 7 hours or more. The reaction solution was cooled to room temperature and concentrated by distilling the solvent under reduced pressure. The concentrated solid was dissolved in dichloromethane, added with an ice water, and extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated solid was added with a mixed solution of ethyl acetate/hexane=1/1 (v/v), and stirred for 2 hours or more at room temperature. The solid thus obtained was filtered under reduced pressure, and washed with a mixed solution of ethyl acetate/hexane=1/1 (v/v). The filtered solid was dried with warm wind in an oven (40° C.) for over 3 hours or more to obtain the title compound (28 g, 55%).

Provenance & Evidence