Chlorosulfonic acid → 1-Chloroisoquinoline-5-sulfonyl chloride

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Reaction Steps

Chlorosulfonic acid (40 mL) is added slowly to 1-chloro-isoquinoline (9.92 g, 60.6 mmol) at 0° C. with stirring under nitrogen. The resultant mixture is heated at 155° C. for 24 hours. Then the mixture is cooled to ambient temperature before it is poured very slowly into ice (200 g). While cold, the mixture is extracted with dichloromethane (300 mL). The organic layer is dried over Na2SO4, filtered and concentrated in vacuo to give 13.6 g (51.9 mmol, yield 86%) of 1-chloro-isoquinoline-5-sulfonyl chloride as a white powder. 1H NMR (CDCl3): δ7.87(t, J=7.5 Hz, 1H), 8.52 (d, J=6.2 Hz, 1H), 8.59 (d, J=6.2 Hz, 1H), 8.62 (d, J=7.5 Hz, 1H), 8.82 (d, J=7.5 Hz, 1H).

Provenance & Evidence