Phosphorus oxychloride → 4-Chloro-7-(2-chlorophenyl)-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700511Notes

Reaction equation

HRID 1700511 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[CH2:22][C:21]2[NH:20][CH:19]=[CH:18][C:17](=O)[C:16]=2[C:15](=[O:24])[CH2:14]1>>[Cl:3][C:17]1[C:16]2[C:15](=[O:24])[CH2:14][CH:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[Cl:6])[CH2:22][C:21]=2[N:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 110656287-(2-Chlorophenyl)-1,4,5,6,7,8-hexahydroquinoline-4,5-dione

Product 1

HCID 183177884-Chloro-7-(2-chlorophenyl)-5,6,7,8-tetrahydroquinolin-5-oneYield 85.9%

Conditions

Temperature
100 °C

Procedure

Under ice-cooling, to phosphorus oxychloride (5.4 g) was added 7-(2-chlorophenyl)-1,4,5,6,7,8-hexahydroquinoline-4,5-dione (0.60 g), and the mixture was stirred at 100° C. for 2 hours and cooled. Under reduced pressure, phosphorus oxychloride was evaporated, and to the residue was added 1N sodium hydroxide solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give colorless crystals of 4-chloro-7-(2-chlorophenyl)-5,6,7,8-tetrahydroquinolin-5-one (0.55 g).

Workup

  1. temperaturecooled
  2. customUnder reduced pressure, phosphorus oxychloride was evaporated
  3. additionto the residue was added 1N sodium hydroxide solution
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f864e17c78394b11bf3094b795c01c1b
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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