Water → Ethyl 4,5-dihydroimidazo[1,2-a]quinoxaline-2-carboxylate

HRID 358024Notes

Reaction equation

HRID 358024 reaction equation
Br.[CH:2]1[N:6]2[C:7]3[C:12]([N:13]=[CH:14][C:5]2=[N:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3.[BH4-].[Na+].O>C(O)C>[CH:2]1[N:6]2[C:7]3[C:12]([NH:13][CH2:14][C:5]2=[N:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 20450288HCID 20450288, compound

Product 1

HCID 13228326Ethyl 4,5-dihydroimidazo[1,2-a]quinoxaline-2-carboxylateYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1.6 g of ethyl imidazo[1,2-a]quinoxaline-2-carboxylate hydrobromide (British patent application Ser. No. 79-26597, in 50 ml of ethanol was added portionwise 0.5 g of sodium borohydride and at the completion of the reaction (tlc), the mixture was poured into 250 ml of water. The mixture was extracted with ethyl acetate and the organic layer was washed with water, dried and evaporated to dryness to obtain 1.2 g (97% yield) of ethyl 4,5-dihydroimidazo[1,2-a]quinoxaline-2-carboxylate melting at 206°-8° C.

Workup

  1. customat the completion of the reaction (tlc)
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-2947693e804a48768ca870206a4868c0
Source dataset
uspto-grants-1984_08
Patent number
US04464373

Reaction notes

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