Thionyl Chloride → Pyridine, 1,2,3,6-tetrahydro-4-(4-chlorophenyl)-1-(4-((7-(trifluoromethyl)-4-quinolinyl)amino)benzoyl)-

HRID 1862915Notes

Reaction equation

HRID 1862915 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH:37]=2)=[CH:32][CH:31]=1>N1C=CC=CC=1>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH2:41][CH2:40][N:39]([C:18](=[O:20])[C:17]3[CH:16]=[CH:15][C:14]([NH:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([C:2]([F:24])([F:1])[F:23])=[CH:4][CH:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:22][CH:21]=3)[CH2:38][CH:37]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 1857174-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridineHCID 13544838HCID 13544838, compound

Product 1

HCID 3054996Pyridine, 1,2,3,6-tetrahydro-4-(4-chlorophenyl)-1-(4-((7-(trifluoromethyl)-4-quinolinyl)amino)benzoyl)-Yield 57%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3.9 g of 4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoic acid and thionyl chloride is allowed to reflux for 41/2 hours. After isolation, the acid chloride is dissolved in 100 ml pyridine and 4.0 g of 4-[4-chlorophenyl]-1,2,5,6-tetrahydropyridine is added. The reaction is stirred overnight and then partitioned between chloroform and aqueous sodium carbonate. The organic phase is dried and concentrated. The residue is crystallized from methylene chloride. The crystals are filtered, washed with ether, and dried to yield 2.99 g (57%) of 4-(4-chlorophenyl)-1,2,5,6-tetrahydro-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]-amino]benzoyl]pyridine, of melting point 225°-226° C.

Workup

  1. temperatureto reflux for 41/2 hours
  2. custompartitioned between chloroform and aqueous sodium carbonate
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customThe residue is crystallized from methylene chloride
  6. filtrationThe crystals are filtered
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-b4109ce4a47a499d80661c8a24207473
Source dataset
uspto-grants-1979_09
Patent number
US04166853

Reaction notes

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