Phosphorus oxychloride → 2-Chloro-8-methylquinoline

HRID 1850300

Reaction equation

HRID 1850300 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[CH:8]=[CH:7]2.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 53251678-methylquinolin-2(1H)-one

Product 1

HCID 215401952-Chloro-8-methylquinolineYield 63%

Conditions

Temperature
60 °C

Procedure

A mixture of 8-methyl-1H-quinolin-2-one (107) (580 mg, 3.6 mmol) and phosphorus oxychloride (5 mL) was stirred at 60° C. overnight. The mixture was then poured onto ice water and extracted with DCM (3×50 mL). The combined extracts were washed with water (2×100 mL) and dried with Na2SO4, and the solvent was removed. The residue was chromatographed on silica gel using 5% to 20% EtOAc in petroleum ether to give product (108) as small colorless crystals (400 mg, 2.3 mmol, 63% yield).

Workup

  1. additionThe mixture was then poured onto ice water
  2. extractionextracted with DCM (3×50 mL)
  3. washThe combined extracts were washed with water (2×100 mL)
  4. dry with materialdried with Na2SO4
  5. customthe solvent was removed
  6. customThe residue was chromatographed on silica gel using 5% to 20% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-79a3c70f3e354e5c8bbbeffcc8f0df80
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Linked notes

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