8-Aminoquinoline → HCID 68183305, compound

HRID 513459Notes

Reaction equation

HRID 513459 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.[CH3:12][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:19][C:18]1[C:13]([CH3:12])=[C:14]([S:20]([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:22])=[O:21])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 5227343-Chloro-2-methylbenzenesulfonyl chloride

Product 1

HCID 68183305HCID 68183305, compoundYield 65%

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-methyl-3-chlorobenzenesulfonyl chloride (180 mg, 0.8 mmol) and DMAP (cat.) gave the title compound (150 mg, 65%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-5d118b59f2424e1a97fce5db7b3a1a57
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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