HCID 178450481, compound → 3-butyryl-8-vinyl-4(1H)-quinolone

HRID 1534488Notes

Reaction equation

HRID 1534488 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20](OC(=O)C1C=CC=CC=1)[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>[C:1]([C:6]1[C:7](=[O:9])[C:19]2[C:14](=[C:15]([CH:20]=[CH2:21])[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 178450481HCID 178450481, compound

Product 1

HCID 102637313-butyryl-8-vinyl-4(1H)-quinolone

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Ethyl 2-butyryl-3-(2-(1-benzoyloxyethyl)phenylamino)-acrylate (70 g, 0.17 mol) was added dropwise to boiling diphenyl ether (700 ml) keeping the reaction temperature above 240° C. The mixture was heated under reflux for 1 hour then cooled rapidly. The mixture was chromatographed (silica gel, dichloromethane +methanol (2%-4%)) to afford the required compound as a light solid (23.2 g, 56%) m.p. 206° C.-8° C.

Workup

  1. customthe reaction temperature above 240° C
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperaturethen cooled rapidly
  5. customThe mixture was chromatographed (silica gel, dichloromethane +methanol (2%-4%))

Sources & evidence

ORD record
ord-c8bad8df04804800b765237b5de84194
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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