2-Nitro-p-toluenesulphonyl chloride → N-(5-chloroquinolin-8-yl)-4-methyl-2-nitrobenzenesulfonamide

HRID 513510Notes

Reaction equation

HRID 513510 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N+:13]([C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[S:23](Cl)(=[O:25])=[O:24])([O-:15])=[O:14]>>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:23]([C:17]2[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=2[N+:13]([O-:15])=[O:14])(=[O:24])=[O:25])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

3

Reactant 2

HCID 1046892-Nitro-p-toluenesulphonyl chloride2×HCID 2248605-Chloroquinolin-8-amine2×

Product 1

HCID 68183028N-(5-chloroquinolin-8-yl)-4-methyl-2-nitrobenzenesulfonamideYield 54%

Procedure

In a similar fashion using route 14 general procedure 26, 5-chloro-8-aminoquinoline (Intermediate 27) (150 mg, 0.84 mmol), 2-nitro-4-methylbenzenesulfonyl chloride (Intermediate 20) (228 mg, 1.26 mmol) gave the title compound (170 mg, 54%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-f04db447f47e4542906d65fcf31e2fdf
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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