Ammonia → 2-Amino-1-carbethoxycarbonylmethyl-3-chloroquinoxalinium bromide

HRID 236324Notes

Reaction equation

HRID 236324 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.ClC1C(Cl)=NC2C(=CC=CC=2)N=1.N.[Br:26][CH2:27][C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(O)C.C(COC)OC>[Br-:26].[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[CH2:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:34]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 166592,3-DichloroquinoxalineHCID 66144Ethyl bromopyruvateHCID 8172743-Chloroquinoxalin-2-amine

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 9 g of 2-amino-3-chloro-quinoxaline [prepared by heating under pressure 2,3-dichloro-quinoxaline and ammonia in ethanol by method of Saikachi et al (Chem. Pharm. Bull. Tokyo (1961), Vol. 9, p. 941], 12 g of ethyl bromopyruvate and 180 ml of dimethoxy ethane was stirred overnight and was filtered to obtain 5.33 of 2-amino-1-carbethoxycarbonylmethyl-3-chloro-quinoxalinium bromide in the form of a pale yellow crystalline solid. The filtrate was held in a refrigerator for 2 days to obtain 2 more crops of 1.20 and 3.62 g of product for a total yield of 10.22 g.

Workup

  1. filtrationwas filtered

Sources & evidence

ORD record
ord-8ed2bc021a354788b2b37cfa14e13b08
Source dataset
uspto-grants-1987_02
Patent number
US04644002

Reaction notes

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