Pyridine → 4-Fluoro-5-methyl-2-nitro-N-quinolin-8-yl-benzenesulfonamide

HRID 513540Notes

Reaction equation

HRID 513540 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9](Cl)(=[O:11])=[O:10])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.[NH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[CH:24][CH:23]=[CH:22]2.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9]([NH:16][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[N:25]=[CH:24][CH:23]=[CH:22]3)(=[O:11])=[O:10])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 113598-AminoquinolineHCID 866697594-Fluoro-5-methyl-2-nitro-benzenesulfonyl chloride2×

Product 1

HCID 681832904-Fluoro-5-methyl-2-nitro-N-quinolin-8-yl-benzenesulfonamideYield 52%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 4-fluoro-5-methyl-2-nitro-benzenesulfonyl chloride (Intermediate 452) (1.6 g, 6.3 mmol), 8-aminoquinoline (700 mg, 4.86 mmol), DMAP (cat.), pyridine (5 ml) and DCM (5 ml) gave the title compound (520 mg, 52%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-fc01fb4d4bd043589581b74e5a82436a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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