HCID 178445048, compound → 3-hexanoyl-8-methoxy-4(1H)-quinolone

HRID 1382263Notes

Reaction equation

HRID 1382263 reaction equation
[C:1]([C:8](=[CH:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[C:9]([O:11]CC)=O)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:1]([C:8]1[C:9](=[O:11])[C:21]2[C:16](=[C:17]([O:22][CH3:23])[CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 1

HCID 178445048HCID 178445048, compound

Product 1

HCID 117780603-hexanoyl-8-methoxy-4(1H)-quinoloneYield 34%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Ethyl 2-hexanoyl-3-(2-methoxyphenylamino)acrylate (18 g, 0.056 mol) was added in portions to boiling diphenyl ether (200 ml) and the mixture heated under reflux for 1 hour. After cooling, the mixture was diluted with petroleum ether, filtered and the solid washed with petroleum ether to give 3-hexanoyl-8-methoxy-4(1H)-quinolone (5.2 g, 33.8%), m.p. 169°-71° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. washthe solid washed with petroleum ether

Sources & evidence

ORD record
ord-176e387657564d6fa975961e5cd49e1c
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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