Ethyl bromopyruvate → 2-Amino-1-carbethoxycarbonylmethyl-3-chloroquinoxalinium bromide

HRID 1578070Notes

Reaction equation

HRID 1578070 reaction equation
[NH2:1][C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:13][CH2:14][C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(COC)OC>[Br-:13].[NH2:1][C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N+:3]=1[CH2:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:21]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 8172743-Chloroquinoxalin-2-amine

Product 1

HCID 140675232-Amino-1-carbethoxycarbonylmethyl-3-chloroquinoxalinium bromide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 9 g of 2-amino-3-chloro-quinoxaline [prepared by heating under pressure in ethanol, ammonia and 2,3-dichlorquinoxaline as taught by Saikachi et al (Chem. Pharm. Bull. Tokyo (1961), Vol. 9, P. 94)], 12 g of ethyl bromopyruvate and 180 ml of dimethoxyethane was stirred overnight and was then vacuum filtered to recover 5.33 g of a pale yellow crystalline solid. The filtrate stood in the refrigerator for several days to recover 1.20g and 3.62 g of the same compound for a total yield of 10.22 g of 2-amino-1-carbethoxycarbonylmethyl-3-chloro-quinoxalinium bromide.

Workup

  1. filtrationvacuum filtered
  2. customto recover 5.33 g of a pale yellow crystalline solid
  3. waitThe filtrate stood in the refrigerator for several days
  4. customto recover 1.20g and 3.62 g of the same compound for a total yield of 10.22 g of 2-amino-1-carbethoxycarbonylmethyl-3-chloro-quinoxalinium bromide

Sources & evidence

ORD record
ord-e539911c83d8485bb0d8220ff14fb00d
Source dataset
uspto-grants-1981_09
Patent number
US04291033

Reaction notes

Loading…