HCID 178450485, compound → HCID 19923016, compound

HRID 1647462Notes

Reaction equation

HRID 1647462 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:29])[C:23]1[CH:28]=[CH:27][CH:26]=[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:29])[C:23]3[CH:24]=[CH:25][CH:26]=[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 178450485HCID 178450485, compound

Product 1

HCID 19923016HCID 19923016, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Diphenyl ether (500 ml) was heated to boiling, ethyl 2-butyryl-3-(2-(benzoyloxymethyl)phenylamino)acrylate (60.5 g, 0.15 mol) added, and heating continued at reflux for 25 minutes. Most of the diphenyl ether was removed by vacuum distillation. Chromatography (silica gel, 0-3% methanol in dichloromethane) and recrystallisation from methanol gave 3-butyryl-8-(benzoyloxymethyl)-4(1H)-quinolone (24.1 g, 45%), m.p. 115°-11°.

Workup

  1. temperatureheating
  2. temperatureat reflux for 25 minutes
  3. customMost of the diphenyl ether was removed by vacuum distillation
  4. customChromatography (silica gel, 0-3% methanol in dichloromethane) and recrystallisation from methanol

Sources & evidence

ORD record
ord-95b9a57b5b3e42b6be2fc2506c5a9c8b
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

Loading…