Phosphorus oxychloride → 2-Chloro-8-(trifluoromethyl)quinoline

HRID 1911769Notes

Reaction equation

HRID 1911769 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=O)[CH:9]=[CH:8]2.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:4]=[CH:5][CH:6]=2)[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 248957428-(Trifluoromethyl)quinolin-2(1H)-one

Product 1

HCID 337782222-Chloro-8-(trifluoromethyl)quinolineYield 33%

Procedure

8-Trifluoromethyl-1H-quinolin-2-one (8.35 g, 39.2 mmol) was taken in a 25 mL RB POCl3 (10 mL) was added, and then refluxed for 1 h. The excess POCl3 was distilled off and ice was added to the reaction mixture. This was stirred for 15 min, the precipitate was filtered off and then dried under vacuum to afford the title compound (3 g, yield: 33%).

Workup

  1. additionwas added
  2. temperaturerefluxed for 1 h
  3. distillationThe excess POCl3 was distilled off
  4. additionice was added to the reaction mixture
  5. filtrationthe precipitate was filtered off
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ced68df90c104877ac009b731c0b2942
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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