8-Aminoquinoline → 4-Methoxy-2-nitro-N-quinolin-8-yl-benzenesulfonamide

HRID 513505Notes

Reaction equation

HRID 513505 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][O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[C:16]([N+:24]([O-:26])=[O:25])[CH:15]=1>>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([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:21])=[O:22])=[C:16]([N+:24]([O-:26])=[O:25])[CH:15]=1

Participants

3

Reactant 2

HCID 113598-AminoquinolineHCID 874524-Methoxy-2-nitrobenzenesulphonyl chloride

Product 1

HCID 167595474-Methoxy-2-nitro-N-quinolin-8-yl-benzenesulfonamideYield 74%

Procedure

In a similar fashion using route 14 general procedure 26, 8-aminoquinoline (220 mg, 2 mmol) and 4-methoxy-2-nitrobenzene-1-sulfonyl chloride (420 mg, 2 mmol) gave the title compound (406 mg, 74%) after purification by column chromatography with heptane/EtOAc (50:50-0:100) gradient elution.

Sources & evidence

ORD record
ord-8eba55832ccc4c20aca7183249b5ec11
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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