Pyridine → 4-methyl-2-nitro-N-quinolin-8-ylbenzenesulfonamide

HRID 513536Notes

Reaction equation

HRID 513536 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: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>C(Cl)Cl>[CH3:12][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:20])=[O:21])=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 113598-AminoquinolineHCID 1046892-Nitro-p-toluenesulphonyl chloride2×

Product 1

HCID 9735044-methyl-2-nitro-N-quinolin-8-ylbenzenesulfonamideYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoquinoline (1.4 g, 9.72 mmol), 4-methyl-2-nitro-benzenesulfonyl chloride (Intermediate 448) (2.97 g, 12.6 mmol), pyridine (7 ml) DMAP (cat.) and DCM (30 ml) gave the title compound (1.5 g, 45%), after purification by column chromatography with n-hexane/EtOAc (90:10) as the eluent.

Sources & evidence

ORD record
ord-af5d315faa6c443982b00e6ef298359c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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