Pyridine → 4-Chloro-2-nitro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide

HRID 513525Notes

Reaction equation

HRID 513525 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:13][C:10]2[CH:11]=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[C:4]3[C:9]=2[N:8]=[CH:7][CH:6]=[CH:5]3)(=[O:25])=[O:24])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 206314-Chloro-2-nitrophenylsulfonyl chloride2×HCID 103531188-Quinolinamine, 5-(trifluoromethyl)-2×

Product 1

HCID 681831454-Chloro-2-nitro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamideYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 5-trifluoromethyl-quinolin-8-ylamine (Intermediate 45) (390 mg, 1.83 mmol), 4-chloro-2-nitrobenzene-1-sulfonyl chloride (Intermediate 454) (565 mg, 2.22 mmol), DMAP(cat) and pyridine (0.3 ml, 5.55 mmol) in DCM (7 ml) gave the title compound (370 mg, 46%) after purification by column chromatography with n-hexane/EtOAc (90:10) as the eluent.

Sources & evidence

ORD record
ord-3a153beaa9a44a26b011791dece1f161
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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