Ammonia → 1-Chloroisoquinoline-5-sulfonamide

HRID 1067240Notes

Reaction equation

HRID 1067240 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH3:16]>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([S:12](=[O:14])(=[O:13])[NH2:16])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 219797811-Chloroisoquinoline-5-sulfonyl chloride

Product 1

HCID 210414581-Chloroisoquinoline-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-chloro-5-chlorosulphonylisoquinoline (613 mg, 2.34 mmol) in methylene chloride saturated with ammonia gas (20 mL) was stirred at RT for 18 h, concentrated in vacuo to a white solid and purified by column chromatography upon silica gel (preabsorbed) using EtOAc-hexanes (1:1) as eluant to give 1-chloro-5-sulphamoylisoquinoline as a white solid (206 mg, 0.85 mmol).

Workup

  1. concentrationconcentrated in vacuo to a white solid
  2. custompurified by column chromatography upon silica gel (preabsorbed)

Sources & evidence

ORD record
ord-5983867db4694066ab27e122182b5941
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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