2-(Benzoyloxymethyl)phenylaminoacrylate → 4-Hydroxyquinoline

HRID 1534478

Reaction equation

HRID 1534478 reaction equation
C(OC[C:11](=[CH:15][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O-:14])=O)(=O)C1C=CC=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[NH:16]1[C:17]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12](=[O:14])[CH:11]=[CH:15]1

Participants

3

Reactant 1

HCID 867454852-(Benzoyloxymethyl)phenylaminoacrylate

Product 1

HCID 691414-HydroxyquinolineYield 110.6%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Diphenyl ether (500 ml) was heated to reflux, ethyl 2-isobutyryl-3-(2-(benzoyloxymethyl)phenylaminoacrylate (29.3 g, 74.1 mmol) added, and heating continued for 15 minutes. The bulk of the diphenyl ether was removed by vacuum distillation, and the residue chromatographed (silica gal, 1%-2.5% methanol in dichloromethane) and recrystallized from ethyl acetate to give 3-isobutyryl-8-benzoyloxymethyl)-4(1H)-quinolone (11.9 g, 46%), m.p. 158°-160°.

Workup

  1. temperatureto reflux
  2. temperatureheating
  3. customThe bulk of the diphenyl ether was removed by vacuum distillation
  4. customthe residue chromatographed (silica gal, 1%-2.5% methanol in dichloromethane)
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-36dd0607720a449fa5bd347b95783b9a
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Linked notes

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