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

HRID 513522Notes

Reaction equation

HRID 513522 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.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([NH:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[N:6]=[CH:5][CH:4]=[C:3]2[C:2]([F:1])([F:14])[F:15])(=[O:27])=[O:26])([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 681832048-Quinolinamine, 4-(trifluoromethyl)-2×

Product 1

HCID 681833412-Nitro-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamideYield 61%

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) (350 mg, 1.65 mmol), 2-nitrobenzenesulfonyl chloride (474 mg, 12.1 mmol), DMAP (cat), pyridine (2 ml) and DCM (5 ml) gave the title compound (400 mg, 60%) after purification by column chromatography with n-hexane/EtOAc (80:20) as the eluent.

Sources & evidence

ORD record
ord-60af7c9cf5e44097951202e81ba56f18
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…