Phosphorus oxychloride → 2-Chloro-6-methoxy-4-methylquinoline

HRID 1018024Notes

Reaction equation

HRID 1018024 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=O)[CH:12]=[C:11]2[CH3:19]>>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([Cl:3])[CH:12]=[C:11]2[CH3:19]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 2200172-Hydroxy-6-methoxy-4-methylquinoline

Product 1

HCID 2247882-Chloro-6-methoxy-4-methylquinolineYield 86.4%

Conditions

Temperature
50 °C

Procedure

A 1-liter, four necked round bottom flask equipped with a mechanical stirrer, thermowatch, and condenser was charged with 630 grams (383 ml) of phosphorous oxychloride. The solution was heated to 50° C. and 6-methoxy-4-methyl-2-quinolone (2) (164.5 g, 0.87 moles) was added over 20 minutes. The reaction mixture was heated to reflux and held there for 2 hours. The hot reaction mixture was slowly poured into ice water (2.5 liters) and the resulting solution cooled to 30° C. The product was removed by suction filtration, washed with water and air dried to yield the title compound 156 g (86.4%); mp 144-145° C. (Lit2 mp 143.5-144.5° C.);

Workup

  1. customA 1-liter, four necked round bottom flask equipped with a mechanical stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. temperaturethe resulting solution cooled to 30° C
  5. customThe product was removed by suction filtration
  6. washwashed with water and air
  7. customdried

Sources & evidence

ORD record
ord-25fbe04363204f56b64076c0373fa86b
Source dataset
uspto-grants-2002_11
Patent number
US06479660B1

Reaction notes

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