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

HRID 513523Notes

Reaction equation

HRID 513523 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:12]2[C:7](=[C:8]([NH2:13])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.[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>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:13][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:7]=2[N:6]=[CH:5][CH:4]=[C:3]3[C:2]([F:1])([F:14])[F:15])(=[O:25])=[O:24])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 206314-Chloro-2-nitrophenylsulfonyl chloride2×HCID 681832048-Quinolinamine, 4-(trifluoromethyl)-2×

Product 1

HCID 681831994-Chloro-2-nitro-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamideYield 60.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 4-trifluoromethyl-quinolin-8-ylamine (Intermediate 469) (325 mg, 1.53 mmol), 4-chloro-2-nitrobenzenesulfonylchloride (Intermediate 454) (507 mg, 1.99 mmol), DMAP (cat.), pyridine (0.5 ml), and DCM (5 ml) gave the title compound (400 mg, 60%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-4165ea35cb9a4699b0a3fd14bbcb6519
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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