Phosphorus oxychloride → HCID 86666254, compound

HRID 533414Notes

Reaction equation

HRID 533414 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[N+:13]([O-])=[CH:12][CH:11]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:12]1[CH:11]=[C:10]([C:3]2[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=2[F:9])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67772997HCID 67772997, compound

Product 1

HCID 86666254HCID 86666254, compound

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-(2,4,6-trifluorophenyl)quinoline-6-carboxylate 1-oxide (1.3 g) and phosphoryl chloride (10 mL) was heated under stirring in an oil bath at 100° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was diluted with water, and then extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 2-chloro-4-(2,4,6-trifluorophenyl)quinoline-6-carboxylate (370 mg).

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe resulting residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d3f24fdb6b9345b5bad019ffbf4d304d
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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