Diphenyl Ether → Ethyl 4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

HRID 73900Notes

Reaction equation

HRID 73900 reaction equation
C(O[C:4](=[O:20])[C:5](=[CH:11][NH:12][C:13]1[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:20])[C:14]2[C:15](=[O:19])[CH2:16][CH2:17][CH2:18][C:13]=2[NH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 12877078diethyl N-(3-oxo-1-cyclohexen-1-yl)-aminomethylenemalonate

Product 1

HCID 12876362Ethyl 4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylateYield 722.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 2-[(3-oxo-cyclohex-1-enylamino)-methylene]-malonic acid diethyl ester (2.8 g, 1 mmol) and diphenylether (20 mL) was refluxed for 15 min. After cooling, n-hexane (80 mL) was added. The resulting solid was isolated via filtration and recrystallized from methanol to give 4,5-dioxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester (1.7 g 72%).

Workup

  1. temperaturewas refluxed for 15 min
  2. temperatureAfter cooling
  3. customThe resulting solid was isolated via filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d7e2103dc6ce46ac8fe5e62d071c8f7e
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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