Phosphorus oxychloride → HCID 57860520, compound

HRID 1947112Notes

Reaction equation

HRID 1947112 reaction equation
O[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[NH:5][C:4](=[O:12])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[NH:5][C:4](=[O:12])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 54682948HCID 54682948, compound

Product 1

HCID 57860520HCID 57860520, compoundYield 17%

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylate (26.0 g, 110 mmol) and phosphorus oxychloride (51.3 mL) was stirred at 130° C. for 1.5 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and ice was added to the residue. The mixture was neutralized with saturated sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed successively with saturated sodium hydrogen carbonate solution, water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was collected by filtration, and washed with ethyl acetate-hexane to give the title compound (4.65 g, 17%) as a white solid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure, and ice
  3. additionwas added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed successively with saturated sodium hydrogen carbonate solution, water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. filtrationThe residue was collected by filtration
  9. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-07248125c2164fb5937bfc0e0da907d4
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

Loading…