6-Methoxy-8-quinolinamine → 2,4-dichloro-N-(6-methoxyquinolin-8-yl)benzenesulfonamide

HRID 513428Notes

Reaction equation

HRID 513428 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH2:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[S:22](Cl)(=[O:24])=[O:23]>>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[S:22]([NH:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2)(=[O:24])=[O:23]

Participants

3

Reactant 2

HCID 70236-Methoxy-8-quinolinamine2×HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-

Product 1

HCID 681833092,4-dichloro-N-(6-methoxyquinolin-8-yl)benzenesulfonamideYield 53%

Procedure

In a similar fashion using route 14 general procedure 26, 6-methoxyquinolin-8-amine (Intermediate 23) (60 mg, 0.35 mmol), 2,4-dichlorobenzenesulfonyl chloride (110 mg, 0.45 mmol) gave the title compound (70 mg, 53%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-88ec89d508c64782a4b0587e39407198
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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