8-Aminoquinoline → 2-Nitro-N-quinolin-8-yl-4-trifluoromethyl-benzenesulfonamide

HRID 513504Notes

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]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[S:25](Cl)(=[O:27])=[O:26])([O-:14])=[O:13]>>[N+:12]([C:15]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:16]=1[S:25]([NH: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)(=[O:27])=[O:26])([O-:14])=[O:13]

Participants

Reactant 2

HCID 113598-Aminoquinoline

HCID 27757802-Nitro-4-(trifluoromethyl)benzene-1-sulfonyl chloride

Product 1

HCID 167599142-Nitro-N-quinolin-8-yl-4-trifluoromethyl-benzenesulfonamideYield 102.4%

Procedure

In a similar fashion using route 14 general procedure 26, 8-aminoquinoline (500 mg, 3 mmol) and 2-nitro-4-(trifluoromethyl)benzene-1-sulfonyl chloride (990 mg, 3 mmol) gave the title compound (1.22 g, 99%).

Sources & evidence

ORD record: ord-6a051b6f14534b7a8da71c95f844c080
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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