Sodium Carbonate → 7-Bromoisoquinoline-5-sulfonyl chloride

HRID 2219197Notes

Reaction equation

HRID 2219197 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+].[Cl:20][S:21](O)(=[O:23])=[O:22]>>[Br:1][C:2]1[CH:3]=[C:4]([S:21]([Cl:20])(=[O:23])=[O:22])[C:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:10]=2[CH:11]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acidHCID 122574417-Bromoisoquinoline

Product 1

HCID 588161467-Bromoisoquinoline-5-sulfonyl chloride

Procedure

7-Bromo-isoquinoline (22.7 g, 109 mmol) is added to a stirred chlorosulfonic acid (230 mL) solution and the resultant mixture is heated at 150° C. under nitrogen for 22 hours. The solution is cooled to ambient temperature and poured very slowly into ice (2 Kg) cooled in a −10° C. bath. While cold, the mixture is adjusted to pH ˜10 with powered Na2CO3 (ca. 200 g) and 5N NaOH. The mixture is extracted with dichloromethane (1 L×2). The combined organic layers are dried over Na2SO4, filtered and concentrated in vacuo to give 16.3 g (crude yield 49%) of 7-bromo-isoquinoline-5-sulfonyl chloride as a tan solid.

Workup

  1. temperaturecooled in a −10° C. bath
  2. extractionThe mixture is extracted with dichloromethane (1 L×2)
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f72c535432954e559579dd236d847cbd
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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