1,3-Diethyl 2-oxopropanedioate → ethyl 3,4-dihydro-7-[1-(1H-imidazol-1-yl)-2-methylpropyl]3-oxo-2-quinoxalinecarboxylate

HRID 1086215Notes

Reaction equation

HRID 1086215 reaction equation
[N:1]1([CH:6]([C:10]2[CH:11]=[C:12]([NH2:17])[C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.O=[C:19]([C:25](OCC)=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[N:1]1([CH:6]([C:10]2[CH:11]=[C:12]3[C:13]([NH:16][C:25](=[O:26])[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:17]3)=[CH:14][CH:15]=2)[CH:7]([CH3:8])[CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 145184264-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamine

Product 1

HCID 19875876ethyl 3,4-dihydro-7-[1-(1H-imidazol-1-yl)-2-methylpropyl]3-oxo-2-quinoxalinecarboxylateYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 15 parts of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-1,2-benzenediamine and 12.5 parts of diethyl 2-oxo-1,3-propanedioate in 80 parts of ethanol was stirred for 2 hours at reflux temperature. The reaction mixture was evaporated and the residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of acetonitrile and ethanol. The product was filtered off and dried, yielding 3.1 parts (14.0%) of ethyl 3,4-dihydro-7-[1-(1H-imidazol-1-yl)-2-methylpropyl]-3-oxo-2-quinoxalinecarboxylate; mp. 229.7° C. (comp. 107).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by column chromatography over silica gel using
  4. additiona mixture of dichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from a mixture of acetonitrile and ethanol
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-ca710a691f064426b163012343375a21
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

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