Ethanol → Dazoquinast

HRID 1155993Notes

Reaction equation

HRID 1155993 reaction equation
[OH-].[Na+].[CH:3]1[N:7]2[C:8]3[C:13]([N:14]=[CH:15][C:6]2=[N:5][C:4]=1[C:16]([O:18]CC)=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=3.C(O)C>O>[CH:3]1[N:7]2[C:8]3[C:13]([N:14]=[CH:15][C:6]2=[N:5][C:4]=1[C:16]([OH:18])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13228325Ethyl imidazo[1,2-a]quinoxaline-2-carboxylate

Product 1

HCID 71146DazoquinastYield 107.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of 1 N sodium hydroxide solution were added to a suspension of 0.63 g of ethyl imidazo-[1,2-a]-quinoxaline-2-carboxylate, 10 ml of ethanol and 30 ml of water and the mixture was refluxed for one hour. The ethanol was evaporated under reduced pressure from the resulting clear yellow solution and the aqueous phase was acidified with concentrated hydrochloric acid. The mixture was filtered to obtain 0.6 g of imidazo-[1,2-a]-quinoxaline-2-carboxylic acid in the form of a buff crystalline solid melting at 274°-275° C.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. customThe ethanol was evaporated under reduced pressure from the resulting clear yellow solution
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-bdeb241fd4e04be7a02e3784ab63d4dd
Source dataset
uspto-grants-1982_06
Patent number
US04333934

Reaction notes

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