Benzenesulfonyl chloride → N-(6-Ethoxy-quinolin-8-yl)-benzenesulfonamide

HRID 513472Notes

Reaction equation

HRID 513472 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH2:14])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH:14][S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:23])=[O:22])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 196093906-Ethoxyquinolin-8-amine2×

Product 1

HCID 68183443N-(6-Ethoxy-quinolin-8-yl)-benzenesulfonamideYield 33%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 6-ethoxyquinolin-8-amine (Intermediate 47) (150 mg, 0.8 mmol), benzenesulfonyl chloride (170 mg, 0.96 mmol) and DMAP (cat.) gave the title compound (85 mg, 33%) after purification by column chromatography with n-hexane/DCM (1:0-0:1) as the eluent and recrystallisation from DCM/n-pentane.

Sources & evidence

ORD record
ord-8a3815cb27004d7c8e03a9e328a81c92
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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