Ammonia → HCID 10355418, compound

HRID 1885186Notes

Reaction equation

HRID 1885186 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].N.P(Cl)(Cl)([Cl:22])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:22])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 10060423HCID 10060423, compound

Product 1

HCID 10355418HCID 10355418, compoundYield 62%

Procedure

3-Butyryl-6-methoxy-4(1H)-quinolone (20 g) was heated under reflux in phosphorus oxychloride for 1 hour. The mixture was cooled, poured onto ice and carefully neutralized with ammonia solution. The mixture was extracted with dichloromethane and the combined extracts washed with sodium hydrogen carbonate solution (×2) and brine. The organic solution was dried, filtered and evaporated to give 3-butyryl-4-chloro-6-methoxy-quinoline (13.3 g, 62%) as an oil which crystallized from ether/petrol; m.p. 73°-75°.

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto ice
  3. extractionThe mixture was extracted with dichloromethane
  4. washthe combined extracts washed with sodium hydrogen carbonate solution (×2) and brine
  5. customThe organic solution was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e9af33d6566b48e399f33c6141faeab7
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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