Ethyl bromopyruvate → Ethyl 5-methoxyimidazo[1,2-a]quinoline-2-carboxylate

HRID 1277953Notes

Reaction equation

HRID 1277953 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:15][C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(COC)OC>[CH3:13][O:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]2[CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:1]=[C:2]2[CH:11]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 98556044-methoxyquinolin-2-amine

Product 1

HCID 13055756Ethyl 5-methoxyimidazo[1,2-a]quinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

350 mg of 2-amino-4-methoxyquinoline [Grout et al., J. C. S. Perkin I, (1973), p. 1314] were dissolved in 10 ml dimethoxyethane and 390 mg of ethyl bromopyruvate were added thereto. The crystalline intermediate thus formed was filtered off, washed with ether and then was dissolved in ethanol. The solution obtained was refluxed for 1 hour and then the solvent was removed under vacuum. The residue was purified by column chromatography (silica gel--chloroform as eluant) and was crystallized from chloroform/ether to give colorless needles of ethyl 5-methoxyimidazo-[1,2-a]-quinoline-2-carboxylate melting at 178°-179° C.

Workup

  1. customThe crystalline intermediate thus formed
  2. filtrationwas filtered off
  3. washwashed with ether
  4. dissolutionwas dissolved in ethanol
  5. customThe solution obtained
  6. temperaturewas refluxed for 1 hour
  7. customthe solvent was removed under vacuum
  8. customThe residue was purified by column chromatography (silica gel--chloroform as eluant)
  9. customwas crystallized from chloroform/ether

Sources & evidence

ORD record
ord-c770da7f72e547628346220c8bfdebcf
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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