8-Aminoquinoline → HCID 51238102, compound

HRID 513442Notes

Reaction equation

HRID 513442 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.[C:12]1([CH3:22])[CH:17]=[CH:16][CH:15]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:13]=1>CN(C1C=CN=CC=1)C>[CH3:22][C:12]1[CH:13]=[C:14]([S:18]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 27345953-Methylbenzenesulphonyl chloride

Product 1

HCID 51238102HCID 51238102, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 8-aminoquinoline (200 mg, 1.38 mmol), m-toluenesulfonyl chloride (260 mg, 1.3 mmol) and DMAP (cat.) gave the title compound (250 mg, 60%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-add3edd2e4e3457eabf776c28115232d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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