Diethyl Oxalate → HCID 135705329, compound

HRID 1112254Notes

Reaction equation

HRID 1112254 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 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 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-f7817caccd8a4b6f800c913003a9bd69
Source dataset
uspto-grants-1978_10
Patent number
US04120962

Reaction notes

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