6-Methoxy-8-quinolinamine → N-(6-methoxyquinolin-8-yl)-4-methyl-2-nitrobenzenesulfonamide

HRID 513509Notes

Reaction equation

HRID 513509 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.[N+:14]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[S:24](Cl)(=[O:26])=[O:25])([O-:16])=[O:15]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH:13][S:24]([C:18]3[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=3[N+:14]([O-:16])=[O:15])(=[O:25])=[O:26])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

3

Reactant 2

HCID 70236-Methoxy-8-quinolinamine2×HCID 1046892-Nitro-p-toluenesulphonyl chloride2×

Product 1

HCID 16759965N-(6-methoxyquinolin-8-yl)-4-methyl-2-nitrobenzenesulfonamideYield 58.2%

Procedure

In a similar fashion using route 14 general procedure 26, 6-methoxyquinolin-8-amine (Intermediate 23) (120 mg, 0.69 mmol) and 4-methyl-2-nitrobenzenesulfonyl chloride (Intermediate 20) (186 mg, 1.03 mmol) gave the title compound (150 mg, 58%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-eda6e5b1ee484c98ac736c33d49651ee
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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