8-Aminoquinoline → 2,4-dichloro-N-quinolin-8-yl-benzenesulfonamide

HRID 513451Notes

Reaction equation

HRID 513451 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[S:20](Cl)(=[O:22])=[O:21]>CN(C1C=CN=CC=1)C>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[S:20]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-

Product 1

HCID 38117162,4-dichloro-N-quinolin-8-yl-benzenesulfonamideYield 103.4%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 8-aminoquinoline (100 mg, 0.69 mmol), 2,4-dichlorobenzenesulfonyl chloride (200 mg, 0.83 mmol) and DMAP (cat.) gave the title compound (252 mg, 100%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-5f46a6126911484fa487b766172d3029
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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