Phosphorus oxychloride → 4-Chloro-2-methylquinoline

HRID 1791944Notes

Reaction equation

HRID 1791944 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1784288112-Methylquinolin-4-ol

Product 1

HCID 779734-Chloro-2-methylquinoline

Procedure

Phosphorus oxychloride (30 mL) was added to 4-hydroxy-2-methylquinoline (10 g), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium carbonate solution was added to the residue under ice-cooling. The mixture was extracted with ethyl acetate. The extract was washed with brine, and concentrated under reduced pressure to give 4-chloro-2-methylquinoline (11.2 g) as a black oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium carbonate solution
  2. additionwas added to the residue under ice-
  3. temperaturecooling
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e2bf5b0eeed4dbba026aa20889124f7
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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