8-Aminoquinoline → HCID 8823686, compound

HRID 513458Notes

Reaction equation

HRID 513458 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[C:18]([Cl:19])=[CH:17][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[C:18]([Cl:19])=[CH:17][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 27342222,3-Dichlorobenzene-1-sulfonyl chloride

Product 1

HCID 8823686HCID 8823686, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoquinoline (100 mg, 0.7 mmol), 2,3-dichlorobenzenesulfonyl chloride (190 mg, 0.8 mmol) and DMAP (cat.) gave the title compound (150 mg, 63%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-d8d7e613b5d34e5aad55259096f8dd47
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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