Dimethylformamide → Isoquinoline-5-sulfonyl chloride hydrochloride

Reaction equation

CN(C=O)C.[CH:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([S:16]([OH:19])(=O)=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1.S(Cl)([Cl:22])=O>C(Cl)Cl>[ClH:22].[CH:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([S:16]([Cl:22])(=[O:19])=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1

Participants

Procedure

Anhydrous DMF (1.5 mL) is added dropwise to a stirred suspension of isoquinoline-5-sulfonic acid (28.3 g, 135 mmol) in thionyl chloride (150 mL, 2.06 mole) at ambient temperature under nitrogen. The resultant mixture is heated to reflux for 2.5 hours. After being cooled to ambient temperature, the mixture is concentrated under vacuum to give a yellowish powder. The powder is suspended in dry CH2Cl2 (200 mL), sonicated, filtered and dried at 40° C. under vacuum to give 29.2 g (111 mmol, 82% yield) of the title compound. 1H NMR (TFA-d1): δ8.48 (t, J=7.9 Hz, 1H), 9.13-9.14 (m, 2H), 9.29 (d, J=7.9 Hz, 1H), 9.57 (d, J=7.0 Hz, 1H), 10.26 (s, 1H).