Ethyl pyruvate → HCID 19875858, compound

HRID 1886358Notes

Reaction equation

HRID 1886358 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[C:9]2[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.O=[C:23]([CH3:29])[C:24](OCC)=[O:25]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[C:9]2[CH:10]=[C:11]3[C:12](=[CH:13][CH:14]=2)[NH:15][C:24](=[O:25])[C:23]([CH3:29])=[N:16]3)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 14500563HCID 14500563, compound

Product 1

HCID 19875858HCID 19875858, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9.1 parts of 4-[(3-chlorophenyl)(1H-imidazol-1-yl)methyl]-1,2-benzenediamine, 3.7 parts of ethyl 2-oxopropanoate and 160 parts of methanol was stirred for 30 minutes at reflux temperature. The reaction mixture was evaporated to dry. The residue was crystallized from a mixture of 36 parts of 2-propanone and 4 parts of methanol. After stirring for 30 minutes at room temperature, the precipitated product was filtered off (the filtrate was set aside) and recrystallized from a mixture of methanol and dichloromethane. The product was filtered off and dried, yielding 3 parts (28.1%) of 6-[(3-chlorophenyl)(1H-imidazol-1-yl)methyl]-3-methyl-2(1H)-quinoxalinone; mp. 270.9° C. (comp. 73). The filtrate (see above) 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 taken up in a mixture of 2-butanone and 2-propanone and the whole was allowed to stand for a few days. The precipitated product was filtered off and dried, yielding 1.4 parts (11.5%) of 7-[(3-chlorophenyl) (1H-imidazol-1-yl)methyl]-3-methyl-2(1H)-quinoxalinone hemihydrate; mp. 201.9° C. (comp. 81).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customto dry
  4. customThe residue was crystallized from a mixture of 36 parts of 2-propanone and 4 parts of methanol
  5. stirringAfter stirring for 30 minutes at room temperature
  6. filtrationthe precipitated product was filtered off (the filtrate
  7. customrecrystallized from a mixture of methanol and dichloromethane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-5364774059374fa3a68de901e8efb51c
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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