Phosphorus oxychloride → HCID 86682946, compound

HRID 1497084Notes

Reaction equation

HRID 1497084 reaction equation
O=P(Cl)(Cl)[Cl:3].[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=O)[C:11]([C:18]#[N:19])=[C:10]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[Cl:3][C:12]1[C:11]([C:18]#[N:19])=[C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([Cl:6])[CH:8]=2)[N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 3525923HCID 3525923, compound

Product 1

HCID 86682946HCID 86682946, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

POCl3 (1.64 g, 1 ml, 10.7 mmol, Eq: 30.1) was added to 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carbonitrile (100 mg, 356 μmol, Eq: 1.00) and the mixture was refluxed for 1 h. The reaction mixture was then allowed to cool to RT, poured onto cold water and extracted with DCM (3×). The combined organic layers were washed with brine, dried with Na2SO4 and evaporated to dryness. The remaining residue was purified by column chromatography (silica gel, DCM/heptane 1:1) to afford the title compound as white solid (81 mg). MS (ESI): 299.0 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. extractionextracted with DCM (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness
  6. customThe remaining residue was purified by column chromatography (silica gel, DCM/heptane 1:1)

Sources & evidence

ORD record
ord-ea4573f9f8a24ad8a4790c72ddec57fe
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

Loading…