Chlorosulfonic acid → 1-Chloroisoquinoline-5-sulfonyl chloride

HRID 2219201Notes

Reaction equation

HRID 2219201 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>>[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:13]([Cl:12])(=[O:15])=[O:14])[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 219797811-Chloroisoquinoline-5-sulfonyl chlorideYield 86%

Procedure

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).

Workup

  1. extractionWhile cold, the mixture is extracted with dichloromethane (300 mL)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7a018f92f94465983b9821306119948
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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