Ethylenediamine → 3-(4-Fluoro-2-methoxyphenyl)-5,6-dihydro-2(1H)-pyrazinone

HRID 1784651Notes

Reaction equation

HRID 1784651 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[C:13]([O:15]CC)=O)=[C:8]([O:19][CH3:20])[CH:7]=1>C(O)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13](=[O:15])[NH:3][CH2:2][CH2:1][N:4]=2)=[C:8]([O:19][CH3:20])[CH:7]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 67117368HCID 67117368, compound

Product 1

HCID 671174173-(4-Fluoro-2-methoxyphenyl)-5,6-dihydro-2(1H)-pyrazinoneYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethylenediamine (0.60 g, 10.0 mmol) was added to a solution of ethyl 2-(4-fluoro-2-methoxyphenyl)-2-oxoacetate (2.26 g, 10.0 mmol) in ethanol (30 ml) and refluxed 4 hr. After removal of the solvent under reduced pressure, residue was washed with ethanol-diethyl ether to give 5,6-dihydro-3-(4-fluoro-2-methoxyphenyl)pyrazinone (1.76 g, 79%).

Workup

  1. temperaturerefluxed 4 hr
  2. customAfter removal of the solvent under reduced pressure, residue
  3. washwas washed with ethanol-diethyl ether

Sources & evidence

ORD record
ord-b94a813eaacb4c7abe63836eb930fc50
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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