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

HRID 513503Notes

Reaction equation

HRID 513503 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.[N+:12]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[S:22](Cl)(=[O:24])=[O:23])([O-:14])=[O:13]>>[F:21][C:19]1[CH:18]=[CH:17][C:16]([S:22]([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:24])=[O:23])=[C:15]([N+:12]([O-:14])=[O:13])[CH:20]=1

Participants

3

Reactant 2

HCID 113598-AminoquinolineHCID 27590464-Fluoro-2-nitrobenzene-1-sulfonyl chloride2×

Product 1

HCID 167599244-Fluoro-2-nitro-N-quinolin-8-yl-benzenesulfonamideYield 105.6%

Procedure

In a similar fashion using route 14 general procedure 26, 8-aminoquinoline (500 mg, 3 mmol) and 2-nitro-4-fluorobenzenesulfonyl chloride (Intermediate 220) (914 mg, 4 mmol) gave the title compound (1.10 g, 91%).

Sources & evidence

ORD record
ord-d9c7fef85bcf44ffa3b46e8243797e03
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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