4-Chlorobenzenesulfonyl chloride → HCID 178527457, compound

HRID 1005701Notes

Reaction equation

HRID 1005701 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[N+:7]([O-:31])[CH:6]=[CH:5]3)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 70297m-Chloroperbenzoic acidHCID 5889916-Aminoisoquinoline

Product 1

HCID 178527457HCID 178527457, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound obtained by the procedure of Example 1, except using 6-aminoisoquinoline (0.5 g, Synthesis, 733 (1975) and 4-chlorobenzenesulfonyl chloride (0.88 g) was dissolved in chloroform (150 ml). Under ice-cooling, m-chloroperbenzoic acid (0.9 g) was added thereto, followed by stirring at room temperature overnight. The solvent was evaporated, and the resulting crystals were washed with diethyl ether, collected by filtration and dried, to give 6-(4-chlorobenzenesulfonylamino)isoquinoline-N-oxide (1.072 g). In acetonitrile (1.5 ml) was dissolved 50 mg of the obtained compound. To the mixture were added trimethyl cyanide (0.08 ml) and triethylamine (0.04 ml), followed by heating under reflux for 3.5 hours. After evaporating the solvent, the residue was purified by silica gel column, to give the title compound (23 mg, 64%) as yellow crystals.

Workup

  1. customThe compound obtained by the procedure of Example 1
  2. temperatureUnder ice-cooling
  3. customThe solvent was evaporated
  4. washthe resulting crystals were washed with diethyl ether
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ffe7eaaeab18441fb9092b4ed8b51541
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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