Diphenyl Ether → HCID 21250045, compound

HRID 1531695

Reaction equation

HRID 1531695 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]2[Cl:17].C([O:20][CH:21]=[C:22]([C:28]([CH3:30])=[O:29])[C:23](OCC)=O)C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:28]([CH:22]1[C:21](=[O:20])[C:3]2[C:2](=[C:11]3[C:6](=[CH:5][CH:4]=2)[C:7]([Cl:17])=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[N:10]3)[N:1]=[CH:23]1)(=[O:29])[CH3:30]

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl esterHCID 21250075HCID 21250075, compound

Product 1

HCID 21250045HCID 21250045, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 8-amino-4-chloro-3-ethoxycarbonylquinoline (0.3 g) and ethyl 2-ethoxymethyleneacetoacetate (Annalen, 1897, 297, 16, 0.25 g) was heated at 90° C. for 2.5 hours. The mixture was cooled to ambient temperature and the resulting solid added to diphenyl ether at reflux. The mixture was refluxed for 45 minutes, and cooled to 60° C. The mixture was diluted with carbon tetrachloride (50 ml) and cooled to ambient temperature with stirring. The mixture was filtered and the solid so obtained purified by flash chromatography on silica using increasingly polar mixtures of methanol and chloroform. The product so obtained was recrystallised from methanol to give 3-acetyl-7-chloro-8-ethoxycarbonyl-4-oxo-3,4-dihydro-1,10-phenanthroline in 29% yield, mp 288-290° C.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperatureat reflux
  3. temperatureThe mixture was refluxed for 45 minutes
  4. temperaturecooled to 60° C
  5. temperaturecooled to ambient temperature
  6. filtrationThe mixture was filtered
  7. customthe solid so obtained
  8. custompurified by flash chromatography on silica using
  9. temperatureincreasingly polar mixtures of methanol and chloroform
  10. customThe product so obtained
  11. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-fc9b0aec85c8416fb9bf4fc9609b7222
Source dataset
uspto-grants-2001_03
Patent number
US06200974B1

Linked notes

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