2-Amino-carbethoxycarbonylmethyl-quinoxalinium bromide → Ethyl imidazo[1,2-a]quinoxaline-2-carboxylate

HRID 236315Notes

Reaction equation

HRID 236315 reaction equation
[Br-].[NH2:2][C:3]1[CH:12]=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N+:4]=1[CH2:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=O>C(O)C>[CH:13]1[N:4]2[C:5]3[C:10]([N:11]=[CH:12][C:3]2=[N:2][C:14]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

3

Reactant 1

HCID 202170592-Amino-carbethoxycarbonylmethyl-quinoxalinium bromide

Product 1

HCID 13228325Ethyl imidazo[1,2-a]quinoxaline-2-carboxylateYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 0.4 g of the product of Step A in 15 ml of ethanol was refluxed for 2 hours and the resulting clear orange solution was concentrated to half its volume. The mixture was filtered to obtain 0.25 g of ethyl imidazo-[1,2-a]-quinoxaline-2-carboxylate as a pale yellow solid which were crystallized from an ether-methanol mixture to obtain the product in the form of soft-white needles melting at 184°-187° C. with decomposition.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationthe resulting clear orange solution was concentrated to half its volume
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-c28d37fa37cc449898444505ef17aa18
Source dataset
uspto-grants-1987_02
Patent number
US04644002

Reaction notes

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