Diethyl (ethoxymethylene)malonate → HCID 21250026, compound

HRID 1416935Notes

Reaction equation

HRID 1416935 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(O[CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19]CC)=O)C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(O)C.CCCCCC>[CH2:25]([O:24][C:22]([CH:16]1[C:17](=[O:19])[C:3]2[C:2](=[C:11]3[C:6](=[CH:5][CH:4]=2)[CH:7]=[CH:8][CH:9]=[N:10]3)[N:1]=[CH:15]1)=[O:23])[CH3:26]

Participants

6

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7583Diphenyl EtherHCID 113598-Aminoquinoline

Product 1

HCID 21250026HCID 21250026, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-aminoquinoline (14.4 g) and diethyl ethoxymethylenemalonate (26 g) in ethanol (100 ml) was heated at reflux for 18 hours. The mixture was cooled, filtered and the solid washed with ethanol. The solid so obtained was added to refluxing diphenyl ether (1000 ml), and the resulting mixture stirred at reflux for 45 minutes. The mixture was cooled to approximately 60° C. and diluted with hexane (500 ml). The mixture was cooled to ambient temperature, filtered and the solid washed with hexane to give 3-ethoxycarbonyl-4-oxo-3,4-dihydro-1,10-phenanthroline in 84% yield, mp 242-244° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe solid washed with ethanol
  6. customThe solid so obtained
  7. additionwas added
  8. temperatureat reflux for 45 minutes
  9. temperatureThe mixture was cooled to ambient temperature
  10. filtrationfiltered
  11. washthe solid washed with hexane

Sources & evidence

ORD record
ord-9a6672c4cea04ecdb1d03fb0a7ddabd3
Source dataset
uspto-grants-1999_06
Patent number
US05916898

Reaction notes

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