Pyridine → 4-Chloro-2-nitro-N-quinolin-8-yl-benzenesulfonamide

HRID 513534Notes

Reaction equation

HRID 513534 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.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([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:20])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 113598-AminoquinolineHCID 206314-Chloro-2-nitrophenylsulfonyl chloride2×

Product 1

HCID 236319584-Chloro-2-nitro-N-quinolin-8-yl-benzenesulfonamideYield 26.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 18 general procedure 27, 8-aminoquinoline (420 mg, 2.91 mmol), 4-chloro-2-nitro-benzenesulfonyl chloride (Intermediate 454) (1.1 g, 4.37 mmol), pyridine (1.5 ml), DMAP (cat.) and DCM (10 ml) gave the title compound (280 mg, 16%) after purification by column chromatography with n-hexane/EtOAc (90:10) elution.

Sources & evidence

ORD record
ord-af73bcfaf5cd4dc6a2c8a695d65511fe
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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