Ethyl bromopyruvate → Ethyl 4-ethoxy-7,8-dichloroimidazo-[1,2-a]-quinoxaline-2-carboxylate

HRID 1578074Notes

Reaction equation

HRID 1578074 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH2:13][CH3:14])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:16])=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.Br[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)C>[CH2:13]([O:12][C:11]1[C:2]2[N:3]([CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:1]=2)[C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([Cl:15])=[C:6]([Cl:16])[CH:5]=2)[CH3:14]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 140675342-Amino-6,7-dichloro-3-ethoxy-quinoxaline

Product 1

HCID 14067535Ethyl 4-ethoxy-7,8-dichloroimidazo-[1,2-a]-quinoxaline-2-carboxylateYield 10.9%

Reagents, catalysts & solvents 1

HCID 6360IsobutaneSolvent

Procedure

A solution of 1 g of the product of Step A, 1 g of ethyl bromopyruvate and 50 ml of dimethylethane was stirred at room temperature for 5 days and the mixture was filtered to recover 0.51 g of a white crystalline solid. The latter was chromatographed over silica gel and was eluted with chloroform to obtain 0.15 g of ethyl 4-ethoxy-7,8-dichloroimidazo-[1,2-a]-quinoxaline-2-carboxylate in the form of a white crystalline solid melting at 256°-258° C.

Workup

  1. filtrationthe mixture was filtered
  2. customto recover 0.51 g of a white crystalline solid
  3. customThe latter was chromatographed over silica gel
  4. washwas eluted with chloroform

Sources & evidence

ORD record
ord-c9554f394b2d4ef79ff2f10aa7868e87
Source dataset
uspto-grants-1981_09
Patent number
US04291033

Reaction notes

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