Phosphorus oxychloride → HCID 86683045, compound

HRID 1497224Notes

Reaction equation

HRID 1497224 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([C:13]#[N:14])=[C:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[CH:16]=1.P(Cl)(Cl)([Cl:26])=O>O>[Cl:26][C:7]1[C:6]([C:13]#[N:14])=[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[CH:16]=2)[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86683044HCID 86683044, compound

Product 1

HCID 86683045HCID 86683045, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-chloro-4-(3-isopropyl-phenyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile (142 mg, 440 μmol, Eq: 1.00) and phosphorus oxychloride (2.02 g, 1.23 ml, 13.2 mmol, Eq: 30) was heated to reflux for 3 h. The reaction mixture was then poured into water and extracted with DCM (3×). The combined organic layers were washed with water and brine, dried with Na2SO4 and evaporated to afford the title compound (126 mg, light yellow solid). MS (ESI): 343.1 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with DCM (3×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-52a384c9e1d240098ca6629b4de5197f
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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