Pyridine → 5-Fluoro-2-nitro-N-quinolin-8-yl-benzenesulfonamide

HRID 513538Notes

Reaction equation

HRID 513538 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.[F:12][C:13]1[CH:14]=[CH:15][C:16]([N+:23]([O-:25])=[O:24])=[C:17]([S:19](Cl)(=[O:21])=[O:20])[CH:18]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([N+:23]([O-:25])=[O:24])=[C:17]([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:20])=[O:21])[CH:18]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 113598-AminoquinolineHCID 129043685-Fluoro-2-nitrobenzene-1-sulfonyl chloride2×

Product 1

HCID 681832775-Fluoro-2-nitro-N-quinolin-8-yl-benzenesulfonamideYield 25%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 18 general procedure 27, 8-aminoquinoline (1.6 g, 11.1 mmol), 5-fluoro-2-nitro-benzenesulfonyl chloride (Intermediate 450) (3.4 g, 14.4 mmol), pyridine (4.48 ml, 55.5 mmol), DMAP (cat.) and DCM (6 ml) gave the title compound (0.95 g, 25%) after purification by column chromatography with n-hexane/DCM (50:50) as the eluent. The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-285ec8de8a3a4bc3ad893bd2d39cae5c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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