Diethyl Ether → Pyrrolo[1,2-a]pyrazin-1(2H)-one

HRID 2248592Notes

Reaction equation

HRID 2248592 reaction equation
C(O[CH:4](OCC)[CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]([NH2:13])=[O:12])C.CCOCC.[OH-].[Na+]>C(O)(=O)C>[C:11]1(=[O:12])[NH:13][CH:4]=[CH:5][N:6]2[CH:10]=[CH:9][CH:8]=[C:7]12

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 15662087HCID 15662087, compound

Product 1

HCID 15662088Pyrrolo[1,2-a]pyrazin-1(2H)-oneYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(2,2-diethoxyethyl)pyrrole-2-carboxamide (3.0 g, 13.2 mmol) was dissolved in glacial acetic acid. The reaction mixture was allowed to reflux and the reaction was continued by thin layer chromatography in a 100% ether system. At the end of the reaction, the reaction mixture was made basic with a 2N solution of sodium hydroxide. The reaction mixture was then extracted with ethyl acetate, washed with a saturated sodium bicarbonate solution, dried over MgSO4 and evaporated. The product was purified by recrystallization in CH2Cl2 -hexane to give the title compound, pyrrolo[1,2-a]pyrazin-1(2H)-one (80%), m.p. 227°-228° C.

Workup

  1. temperatureto reflux
  2. customAt the end of the reaction
  3. extractionThe reaction mixture was then extracted with ethyl acetate
  4. washwashed with a saturated sodium bicarbonate solution
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe product was purified by recrystallization in CH2Cl2 -hexane

Sources & evidence

ORD record
ord-5905f13c88294fafa88c9fdeb0458e8e
Source dataset
uspto-grants-1991_08
Patent number
US05041442

Reaction notes

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