4-Chlorobenzenesulfonyl chloride → HCID 178527457, compound

HRID 1173144Notes

Reaction equation

HRID 1173144 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, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound obtained using 6-aminoisoquinoline (0.5 g, Synthesis, 733 (1975)) and 4-chlorobenzenesulfonyl chloride (0.88 g) in the same method as in Synthetic Example 1b 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 in the amount of the product, to which were then 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
  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-13f700ae6fc2456ea9d0dccad01fcc97
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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