Ammonia → 1,4-Dichloro-7-sulphamoylisoquinoline

HRID 1067244Notes

Reaction equation

HRID 1067244 reaction equation
Cl[S:2]([C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:16])=[CH:10][N:11]=[C:12]2[Cl:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH3:17]>>[Cl:15][C:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([S:2](=[O:4])(=[O:3])[NH2:17])[CH:14]=2)[C:9]([Cl:16])=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chloride

Product 1

HCID 166586321,4-Dichloro-7-sulphamoylisoquinoline

Procedure

7-chlorosulphonyl-1,4-dichloroisoquinoline (110 mg, 0.37 mmol) was dissolved in a solution of saturated methanolic ammonia (NH3) (10 mL) and the solution stirred at room temperature for 1.5 hours. The solvents were evaporated in vacuo and the residue was azeotroped with CH2Cl2 and then partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4) and evaporated in vacuo to give 1,4-dichloro-7-sulphamoylisoquinoline (98 mg, 0.35 mmol) as a white solid.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue was azeotroped with CH2Cl2
  3. custompartitioned between EtOAc and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-2cafeccf2f0a4c2499c528193bf31747
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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