Diphenyl Ether → 3-butyryl-8-acetyl-4(1H)-quinolone

HRID 1885172

Reaction equation

HRID 1885172 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:22])[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]([C:20](=[O:22])[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 178450482HCID 178450482, compound

Product 1

HCID 103777553-butyryl-8-acetyl-4(1H)-quinoloneYield 70.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 2-butyryl-3-(2-acetylphenylamino)acrylate (14.8 g, 48.8 mmol) was added to boiling diphenyl ether (50 ml) and heated at reflux for 3.5 hours. After cooling, the solution was poured into ether, and the solid filtered off and washed with ether to obtain 3-butyryl-8-acetyl-4(1H)-quinolone (8.8 g), contaminated with some diphenyl ether. This material was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3.5 hours
  3. temperatureAfter cooling
  4. filtrationthe solid filtered off
  5. washwashed with ether

Sources & evidence

ORD record
ord-b0f96a80b7ba468191ba8632e0f3bb51
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Linked notes

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