HCID 178471922, compound → 3-isobutyryl-8-methoxy-4(1H)-quinolone

HRID 1382332Notes

Reaction equation

HRID 1382332 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])[CH:2]([CH3:4])[CH3:3]>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]([O:20][CH3:21])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=[O:5])[CH:2]([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 178471922HCID 178471922, compound

Product 1

HCID 102639013-isobutyryl-8-methoxy-4(1H)-quinoloneYield 52.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Ethyl 2-isobutyryl-3-(2-methoxyphenylamino)acrylate (18.8 g, 0.065 mol) was added in portions to boiling diphenyl ether (150 ml). The mixture was heated under reflux for 30 minutes, cooled, and diluted with petroleum ether (500 ml). Filtration of the mixture gave 3-isobutyryl-8-methoxy-4(1H)-quinolone as a light brown solid (8.32 g, 52.2%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturecooled
  4. filtrationFiltration of the mixture

Sources & evidence

ORD record
ord-d3a21179271742f48d65cb7242b33020
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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