Trifluoroacetic acid → HCID 67339276, compound

Participants

Reaction Steps

Alternative preparation to Example 5: To a round bottom flask fitted with reflux condenser was added 1-chloro-6-methyl-5-nitroisoquinoline (13.0 g, 50 mmol), and 2-methyl-5-benzothiazolamine (8.63 g, 52.5 mmol). Nitrogen atmosphere was applied, and the mixture was treated with isopropanol (111 mL). The reaction vessel contents were stirred to obtain a slurry. TFA (11.35 mL, 150 mmol) was then added slowly and the contents of the flask were heated to reflux. The reaction was held at reflux for 17 h, then removed from heat. The reaction mixture was filtered on a fritted funnel at room temperature. The solid was reslurried in refluxing isopropanol (222 mL) for 18 h. The slurry was then cooled to room temperature and filtered. The resulting yellow solid was then dried under vacuum at 55° C. overnight to 17.77 g 6-methyl-N1-(2-methylbenzo[d]thiazol-5-yl)isoquinoline-1,5-diamine hydrochloride (91% yield). MS (M+H)+ 351.

Provenance & Evidence