Ethyl bromopyruvate → HCID 12763970, compound

HRID 1277961Notes

Reaction equation

HRID 1277961 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:16][C:17](=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(COC)OC>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]2[CH:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:1]=[C:2]2[CH:11]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 14067409HCID 14067409, compound

Product 1

HCID 12763970HCID 12763970, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.3 g of 2-amino-4-chloro-7-methoxyquinoline were dissolved in 20 ml of dimethoxyethane and 1.3 g of ethyl bromopyruvate were added thereto. The mixture was stirred at room temperature for 2 hours and the crystalline intermediate thus formed was filtered off, washed with ether and then was dissolved in 20 ml of ethanol. The resultant solution was refluxed for 3 hours and ethyl 5-chloro-8-methoxyimidazo-[1,2-a]-quinoline-2-carboxylate melting at 215°-216° C. was isolated by the procedure of Example 9.

Workup

  1. customthe crystalline intermediate thus formed
  2. filtrationwas filtered off
  3. washwashed with ether
  4. dissolutionwas dissolved in 20 ml of ethanol
  5. temperatureThe resultant solution was refluxed for 3 hours

Sources & evidence

ORD record
ord-9548466e723e485da6095f09e84db62b
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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