Ethyl bromopyruvate → HCID 12763962, compound

HRID 1277954Notes

Reaction equation

HRID 1277954 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:10][C:11]1[CH:20]=[C:19]([Cl:21])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1>C(COC)OC>[Cl:21][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]2[CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:10]=[C:11]2[CH:20]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 140674074-Chloroquinolin-2-amine

Product 1

HCID 12763962HCID 12763962, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

4 g of ethyl bromopyruvate were added to a solution of 2 g of 2-amino-4-chloroquinoline [Hardman et al C.S., (1958), p. 614] in 40 ml of dimethoxyethane and the mixture obtained was allowed to stand at room temperature for 30 minutes. The quaternary salt thus precipitated was filtered off, washed with ether and then was dissolved in ethanol. The solution obtained was heated at reflux for 1 hour and then the ethanol was removed under vacuum. The residue was dissolved in chloroform and the solution was washed with dilute sodium carbonate solution and water, was decolorized with charcoal and the solvent was evaporated to leave a white solid. This solid was recrystallized from methanol to obtain fine white needles of ethyl 5-chloroimidazo-[1,2-a]-quinoline-2-carboxylate melting at 169°-170° C.

Workup

  1. customthe mixture obtained
  2. customThe quaternary salt thus precipitated
  3. filtrationwas filtered off
  4. washwashed with ether
  5. dissolutionwas dissolved in ethanol
  6. customThe solution obtained
  7. temperaturewas heated
  8. temperatureat reflux for 1 hour
  9. customthe ethanol was removed under vacuum
  10. dissolutionThe residue was dissolved in chloroform
  11. washthe solution was washed with dilute sodium carbonate solution and water
  12. customthe solvent was evaporated
  13. customto leave a white solid
  14. customThis solid was recrystallized from methanol

Sources & evidence

ORD record
ord-423d04a1e90040658dd7209ea387bded
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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