Diphenyl Ether → Ethyl 4-oxo-4H-quinolizine-3-carboxylate

HRID 255585Notes

Reaction equation

HRID 255585 reaction equation
C(O[CH:4]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH:5]([C:11](OCC)=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH2:9]([O:8][C:6]([C:5]1[C:11](=[O:12])[N:18]2[C:17]([CH:22]=[CH:21][CH:20]=[CH:19]2)=[CH:16][CH:4]=1)=[O:7])[CH3:10]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 15632050HCID 15632050, compound

Product 1

HCID 4615166Ethyl 4-oxo-4H-quinolizine-3-carboxylateYield 86.5%

Conditions

Temperature
250 °C

Procedure

A mixture of ethyl 3-ethoxy-2-ethoxycarbonyl-4-(2-pyridyl)butyrate (18.9 g), diphenyl (48.85 g) and diphenyl ether (135.8 g) was heated to 250° C. for 40 minutes. The reaction mixture was cooled to ambient temperature and chromatographed on silica gel (Merck 70-230 mesh, 620 g) eluting with hexane and then a mixture of ethanol and chloroform (1:49) to give a crude oil, which was crystallized from a mixture of ether and hexane (1:1) to give 3-ethoxycarbonyl-4H-quinolizin-4-one (11.48 g) as yellow crystal.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customchromatographed on silica gel (Merck 70-230 mesh, 620 g)
  3. washeluting with hexane
  4. additiona mixture of ethanol and chloroform (1:49)
  5. customto give a crude oil, which
  6. customwas crystallized from a mixture of ether and hexane (1:1)

Sources & evidence

ORD record
ord-05fa56cab460453f9d891862269afff8
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Reaction notes

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