HCID 178450484, compound → 3-butyryl-8-methyl-4(1H)-quinolone

HRID 1382286Notes

Reaction equation

HRID 1382286 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[C:7]([O:9]CC)=O)(=[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:9])[C:19]2[C:14](=[C:15]([CH3:20])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 178450484HCID 178450484, compound

Product 1

HCID 103765253-butyryl-8-methyl-4(1H)-quinoloneYield 98.1%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Ethyl 2-butyryl-3-(2-methylphenylamino)acrylate (66 g, 0.24 mol) was added in portions to boiling diphenyl ether (500 ml), then heated at reflux for 1.5 hours. After partial cooling, the mixture was poured into high boiling petroleum ether. Filtration and washing with petroleum ether gave 3-butyryl-8-methyl-4(1H)-quinolone (54 g) as a pale solid, which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. additionAfter partial cooling, the mixture was poured
  4. filtrationFiltration
  5. washwashing with petroleum ether

Sources & evidence

ORD record
ord-5cd39ab4f86047e5bf7ed6b03010d0c3
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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