Phosphorus oxychloride → HCID 67775454, compound

HRID 533413Notes

Reaction equation

HRID 533413 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[N:4][C:5]2[C:10]([C:11]=1O)=[CH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=2.P(Cl)(Cl)([Cl:21])=O>>[Cl:1][C:2]1[C:3]([CH3:18])=[N:4][C:5]2[C:10]([C:11]=1[Cl:21])=[CH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178468669HCID 178468669, compound

Product 1

HCID 67775454HCID 67775454, compound

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 3-chloro-4-hydroxy-2-methylquinoline-6-carboxylate (629 mg) and phosphoryl chloride (2 mL) was stirred in an oil bath at 100° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was diluted with water, and 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 ethyl 3,4-dichloro-2-methylquinoline-6-carboxylate (454 mg).

Workup

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

Sources & evidence

ORD record
ord-03232d894a3e4c5293168e85f6cfe0a0
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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