Diphenyl Ether → 4(1H)-Quinolinone, 8-methoxy-3-(1-oxobutyl)-

HRID 1382310Notes

Reaction equation

HRID 1382310 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[C:7]([O:9]CC)=O)(=[O:5])[CH2:2][CH2:3][CH3:4].C1(OC2C=CC=CC=2)C=CC=CC=1>CCOCC>[C:1]([C:6]1[C:7](=[O:9])[C:19]2[C:14](=[C:15]([O:20][CH3:21])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 178450493HCID 178450493, compound

Product 1

HCID 103321024(1H)-Quinolinone, 8-methoxy-3-(1-oxobutyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 2-butyryl-3-(2-methoxyphenylamino)acrylate (15.50 g, 0.053 mol) was added in portions to boiling diphenyl ether (400 ml) and the mixture heated under reflux for 1.5 hours. After cooling, the solution was diluted with ether and petroleum ether, filtered, and the solid washed with petroleum ether to give 3-butyryl-8-methoxy-4-(1H)-quinolone as light grey crystals (13.46 g, 63.1%, m.p. 200°-202°.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. washthe solid washed with petroleum ether

Sources & evidence

ORD record
ord-e313ef4e13094df7acc22cc0919c20d8
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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