4-Cyanobenzenesulfonyl chloride → 4-[6-(4-Trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-benzonitrile

HRID 1842030Notes

Reaction equation

HRID 1842030 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](S(Cl)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[F:13][C:14]([F:32])([F:31])[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH2:26][CH2:25][CH2:24]3)=[CH:17][CH:16]=1>N1C=CC=CC=1>[F:32][C:14]([F:13])([F:31])[C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 394974-Cyanobenzenesulfonyl chloride2×HCID 120011176-[4-(Trifluoromethyl)phenyl]-1,2,3,4-tetrahydroquinoline

Product 1

HCID 670173184-[6-(4-Trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

582 mg of commercially available 4-cyano-benzenesulfonyl chloride were dissolved in 5 ml pyridine. Then 400 mg 6-(4-Trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-quinoline were added and the mixture was stirred at room temperature for thirty minutes. Then 290 mg of commercially available 4-cyano-benzenesulfonyl chloride were added and the mixture was stirred at room temperature for additional two hours. Then the solvent was removed in vacuo and the residue was purified by chromatography on silica gel to obtain 307 mg of 4-[6-(4-Trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-benzonitrile.

Workup

  1. stirringthe mixture was stirred at room temperature for additional two hours
  2. customThen the solvent was removed in vacuo
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-241f609b495949c1994e997eb8be09ce
Source dataset
uspto-grants-2015_02
Patent number
US08946212B2

Reaction notes

Loading…