4-Chloro-2-nitrophenylsulfonyl chloride → 4-Chloro-N-(5-cyano-quinolin-8-yl)-2-nitro-benzenesulfonamide

HRID 513544Notes

Reaction equation

HRID 513544 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]#[N:13])=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[C:17]([N+:25]([O-:27])=[O:26])[CH:16]=1.[H-].[Na+]>C1COCC1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:12]#[N:13])=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)(=[O:23])=[O:22])=[C:17]([N+:25]([O-:27])=[O:26])[CH:16]=1

Participants

5

Reactant 3

HCID 206314-Chloro-2-nitrophenylsulfonyl chloride2×HCID 24758Sodium hydrideHCID 681833618-Aminoquinoline-5-carbonitrile2×

Product 1

HCID 681834404-Chloro-N-(5-cyano-quinolin-8-yl)-2-nitro-benzenesulfonamideYield 30.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar fashion using route 14 general procedure 58, 8-aminoquinoline-5-carbonitrile (Intermediate 472) (100 mg, 0.5 mmol), 4-chloro-2-nitrobenzenesulfonyl chloride (Intermediate 454) (166 mg, 0.65 mmol), NaH (60% dispersion in mineral oil, 26 mg, 0.65 mmol) and THF (2 ml) gave the title compound (60 mg, 26%) after purification by column chromatography with n-hexane/DCM (50:50) as the eluent.

Sources & evidence

ORD record
ord-09570fe646544126ad256b541dbfdae6
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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