Phosphorus oxychloride → HCID 53728089, compound

HRID 2192803Notes

Reaction equation

HRID 2192803 reaction equation
O[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178468540HCID 178468540, compound

Product 1

HCID 53728089HCID 53728089, compound

Procedure

Ethyl 2-hydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylate (3.40 g) was dissolved in phosphorus oxychloride (30 ml), and the mixture was stirred with heating to reflux for 10 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (50:50-100:0) was concentrated under reduced pressure to give the object compound (3.68 g).

Workup

  1. temperaturewith heating
  2. temperatureto reflux for 10 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. washthe fraction eluted with ethyl acetate-hexane (50:50-100:0)
  10. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-6bc5a9dba7f34320bf5d8a151d74bdba
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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