HCID 178450486, compound → 3-butyryl-8-(4-methoxybenzoyloxymethyl)-4(1H)-quinolone

HRID 1647439Notes

Reaction equation

HRID 1647439 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[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]([CH2:20][O:21][C:22](=[O:31])[C:23]3[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)[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 178450486HCID 178450486, compound

Product 1

HCID 103175623-butyryl-8-(4-methoxybenzoyloxymethyl)-4(1H)-quinoloneYield 54%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Ethyl 2-butyryl-3-(2-(4-methoxybenzoyloxymethyl)-phenylamino)acrylate (12.2 g, 28.7 mmol) was added in portions to boiling diphenyl ether (200 ml), then heated at reflux for 30 minutes. Most of the diphenyl ether was distilled off in vacuo, and the residue triturated with ether to give 3-butyryl-8-(4-methoxybenzoyloxymethyl)-4(1H)-quinolone (5.85 g, 54%), m.p. 156°-162°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 minutes
  3. distillationMost of the diphenyl ether was distilled off in vacuo
  4. customthe residue triturated with ether

Sources & evidence

ORD record
ord-299c19408b324773a6856aa2c867a345
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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