Diethyl Oxalate → HCID 135705328, compound

HRID 2163581Notes

Reaction equation

HRID 2163581 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=O.[F:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[C:17]([C:23]([NH2:25])=[O:24])[C:18]([NH2:22])=[N:19]2)=[CH:14][CH:13]=1>CCCCCC>[F:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[C:17]3[C:23](=[O:24])[NH:25][C:2]([C:1]([O:8][CH2:9][CH3:10])=[O:7])=[N:22][C:18]3=[N:19]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 22752815HCID 22752815, compound

Product 1

HCID 135705328HCID 135705328, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
160 °C

Procedure

Diethyl oxalate (47.5 g., 0.326 mole) and 7-fluoro-2-aminoquinoline-3-carboxamide (3.7 g., 0.015 mole) are mixed together and heated at 160° C. for seven hours. The reaction mixture is cooled to room temperature, hexane (300 ml.) added, and the brown solid which precipitates filtered off, and washed with hexane (60 ml.). It is then slurried in hot chloroform (250 ml.) and the insoluble material removed by filtration. The hot filtrate is decolorized with charcoal, filtered and dried (Na2SO4). The light brown solid which precipitates upon cooling is filtered off and recrystallized from isopropyl alcohol. Yield = 1.04 g. (29.2%) of the title ethyl ester. M.P. 248°-251° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe brown solid which precipitates
  3. filtrationfiltered off
  4. washwashed with hexane (60 ml.)
  5. customthe insoluble material removed by filtration
  6. filtrationfiltered
  7. dry with materialdried (Na2SO4)
  8. customThe light brown solid which precipitates
  9. temperatureupon cooling
  10. filtrationis filtered off
  11. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-48405dd6323440e19e495c4aef5714ed
Source dataset
uspto-grants-1979_01
Patent number
US04134981

Reaction notes

Loading…