Pyridine → N-(5-Chloro-quinolin-8-yl)-2-nitro-benzenesulfonamide

HRID 513515Notes

Reaction equation

HRID 513515 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]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23])([O-:15])=[O:14].N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N+:13]([O-:15])=[O:14])(=[O:23])=[O:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 2248605-Chloroquinolin-8-amine2×

Product 1

HCID 68183417N-(5-Chloro-quinolin-8-yl)-2-nitro-benzenesulfonamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 26, 5-chloro-quinolin-8-ylamine (Intermediate 27) (380 mg, 2.13 mmol), 2-nitrobenzene-1-sulfonyl chloride (566 mg, 2.56 mmol), pyridine (0.34 ml, 4.26 mmol) and DCM (12 ml) gave the title compound (610 mg, 79%) after purification by column chromatography with n-hexane/DCM (1:1) as the eluent.

Sources & evidence

ORD record
ord-22d9b719a2724a2c9f738fc071deb19d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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