Phosphorus oxychloride → 2-Chloro-6,7-dimethylquinoline-3-carbonitrile

HRID 2413151Notes

Reaction equation

HRID 2413151 reaction equation
[C:1]([C:3]1[C:4](=O)[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH3:13])=[C:8]([CH3:14])[CH:7]=2)#[N:2].P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:4]1[C:3]([C:1]#[N:2])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([CH3:14])=[C:9]([CH3:13])[CH:10]=2)[N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 133714281,2-Dihydro-6,7-dimethyl-2-oxo-3-quinolinecarbonitrile

Product 1

HCID 133714332-Chloro-6,7-dimethylquinoline-3-carbonitrile

Procedure

A mixture was prepared from 67.5 g of 3-cyano-6,7-dimethyl-2(1H)-quinolinone and 340 ml of phosphoryl chloride and this was heated at reflux for 18 hours. The mixture was cooled, excess phosphoryl chloride was removed by vacuum evaporation, and the residue was carefully added to water with vigorous stirring. The solid which formed was separated by filtration and recrystallized from methylene chloride to give 2-chloro-3-cyano-6,7-dimethylquinoline melting at about 189°-190° C.

Workup

  1. temperaturethis was heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. customexcess phosphoryl chloride was removed by vacuum evaporation
  5. additionthe residue was carefully added to water with vigorous stirring
  6. customThe solid which formed
  7. customwas separated by filtration
  8. customrecrystallized from methylene chloride

Sources & evidence

ORD record
ord-0d595101550b4d03b90c8c286d071b75
Source dataset
uspto-grants-1985_01
Patent number
US04496569

Reaction notes

Loading…