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

HRID 513537Notes

Reaction equation

HRID 513537 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.[CH3:12][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>C(Cl)Cl>[CH3:12][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

5

Reactant 3

HCID 1049PyridineHCID 113598-AminoquinolineHCID 55279901HCID 55279901, compound2×

Product 1

HCID 681831575-Methyl-2-nitro-N-quinolin-8-yl-benzenesulfonamideYield 12.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoquinoline (0.350 g, 2.4 mmol), 5-methyl-2-nitro-benzenesulfonyl chloride (Intermediate 449) (0.86 g, 3.6 mmol), pyridine (1 ml) DMAP (cat) and DCM (5 ml) gave the title compound (100 mg, 12%) after purification by column chromatography with n-hexane/EtOAc (10:90) as the eluent. The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-fbed180d70bf4e08b39c9a588b84731e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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