Phosphorus oxychloride → 4-Chloro-2-methyl-7-(trifluoromethyl)quinoline

HRID 333957Notes

Reaction equation

HRID 333957 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10](O)[C:9]2[C:4](=[CH:5][C:6]([C:13]([F:16])([F:15])[F:14])=[CH:7][CH:8]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:19]>>[CH3:1][C:2]1[CH:11]=[C:10]([Cl:19])[C:9]2[C:4](=[CH:5][C:6]([C:13]([F:16])([F:15])[F:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428818HCID 178428818, compound

Product 1

HCID 47368054-Chloro-2-methyl-7-(trifluoromethyl)quinoline

Procedure

2-Methyl-7-(trifluoromethyl)quinolin-4-ol (1 g, 4.4 mmol) was heated in phosphoroxychloride (3 ml) for under reflux for one hour. The mixture was poured on ice and left at 4° C. overnight. The mixture was extracted with ethylacetate, the organic phase was washed with water, dried over sodium sulfate and evaporated to dryness under reduced pressure to yield 1.1 g (4.4 mmol, quantitative) which were used directly in the next step.

Workup

  1. temperatureunder reflux for one hour
  2. additionThe mixture was poured on ice
  3. extractionThe mixture was extracted with ethylacetate
  4. washthe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customto yield 1.1 g (4.4 mmol, quantitative) which

Sources & evidence

ORD record
ord-6e7951443fa949b38d2f1f5c4cb76a86
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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