Dimethylformamide → 2-Chloro-4-(trifluoromethyl)quinoline

HRID 513732Notes

Reaction equation

HRID 513732 reaction equation
CN(C=O)C.[F:6][C:7]([F:20])([F:19])[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10](=O)[CH:9]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:10]1[CH:9]=[C:8]([C:7]([F:20])([F:19])[F:6])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 27593472-Hydroxy-4-(trifluoromethyl)quinoline

Product 1

HCID 27829122-Chloro-4-(trifluoromethyl)quinolineYield 29%

Conditions

Temperature
90 °C

Procedure

DMF (cat.) was added to a solution of 4-trifluoromethyl-1H-quinolin-2-one 465 (160 mg, 0.75 mmol) in POCl3 (2 ml) and the mixture was heated at 90° C. for 1 h. After cooling, the mixture was concentrated in vacuo and the residue was poured into an ice cold solution of NaHCO3 solution. The aqueous phase was extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound (50 mg, 29%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. additionthe residue was poured into an ice cold solution of NaHCO3 solution
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79f1f1d9d02242dda64edece07364eac
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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