8-Aminoquinoline → N-(Quinolin-8-yl)-3-trifluoromethylbenzenesulfonamide

HRID 513453Notes

Reaction equation

HRID 513453 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.[F:12][C:13]([F:25])([F:24])[C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1>CN(C1C=CN=CC=1)C>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][S:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:24])[F:25])[CH:15]=2)(=[O:22])=[O:21])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 3863015N-(Quinolin-8-yl)-3-trifluoromethylbenzenesulfonamideYield 100.4%

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), 3-trifluoromethylbenzenesulfonyl chloride (200 mg, 0.83 mmol) and DMAP (cat.) gave the title compound (244 mg, 100%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-2da3a563d63549a68eebb40c497bc519
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…