Diethyl Oxalate → HCID 135705329, compound

HRID 1283167Notes

Reaction equation

HRID 1283167 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=O.[Cl:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[C:15]([C:23]([NH2:25])=[O:24])[C:16]([NH2:22])=[N:17]2>CCCCCC>[Cl:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[C:15]1[C:23](=[O:24])[NH:25][C:2]([C:1]([O:8][CH2:9][CH3:10])=[O:7])=[N:22][C:16]1=[N:17]2

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 22752829HCID 22752829, compound

Product 1

HCID 135705329HCID 135705329, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Diethyl oxalate (350 ml.) and 5-chloro-2-aminoquinoline-3-carboxamide (5.9 g., 0.0267 mole) are heated together at 170° C. for 4 hours. By-product water and ethanol are distilled from the reaction mixture. The dark reaction mixture is cooled, treated with hexane (300 ml.) and filtered. The brown solid is dissolved in methylene chloride:ethanol (1:1), decolorized with charcoal and concentrated to give a tan solid. The solid is recrystallized from methylene chloride-hexane. It is purified further by chromatography on silica gel using methylene chloride:ethanol (9:1) as eluant. The product, recovered by evaporation of the eluate, is recrystallized from methylene chloride-ethanol. Yield = 0.756 g. (9.3%). M.P. 278°-279° C. (dec.).

Workup

  1. distillationBy-product water and ethanol are distilled from the reaction mixture
  2. customThe dark reaction mixture
  3. temperatureis cooled
  4. filtrationfiltered
  5. dissolutionThe brown solid is dissolved in methylene chloride:ethanol (1:1)
  6. concentrationconcentrated
  7. customto give a tan solid
  8. customThe solid is recrystallized from methylene chloride-hexane
  9. customIt is purified further by chromatography on silica gel
  10. customThe product, recovered by evaporation of the eluate,
  11. customis recrystallized from methylene chloride-ethanol

Sources & evidence

ORD record
ord-f6f014df131941509b25096740fd80db
Source dataset
uspto-grants-1976_08
Patent number
US03974161

Reaction notes

Loading…