Diphenyl Ether → 3-butyryl-6-benzoyloxy-8-methoxy-4(1H)-quinolone

HRID 1885192Notes

Reaction equation

HRID 1885192 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][C:15]=1[O:29][CH3:30])[C:7](OCC)=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].C1(OC2C=CC=CC=2)C=CC=CC=1>>[C:1]([C:6]1[C:7](=[O:8])[C:19]2[C:14](=[C:15]([O:29][CH3:30])[CH:16]=[C:17]([O:20][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=2)[NH:13][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 178450503HCID 178450503, compound

Product 1

HCID 104065273-butyryl-6-benzoyloxy-8-methoxy-4(1H)-quinoloneYield 92.6%

Procedure

Ethyl 2-butyryl-3-(4-benzoyloxy-2-methoxyphenylamino)acrylate (22 g) was added portionwise to boiling diphenyl ether and heated under reflux for 45 minutes. When cool, the mixture was chromatographed (silica gel, 2% methanol in dichloromethane) to give 3-butyryl-6-benzoyloxy-8-methoxy-4(1H)-quinolone as a light brown solid (18.1 g, 92%), m.p. 102°-4°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 45 minutes
  3. temperatureWhen cool
  4. customthe mixture was chromatographed (silica gel, 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ce5d07007ca5408aac654772dd235fa0
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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