Acetic Acid → HCID 58575390, compound

HRID 1189448Notes

Reaction equation

HRID 1189448 reaction equation
Cl[C:2]1[C:3]([NH:16][NH2:17])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.C(O)(=[O:30])C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]2[N:4]3[C:5]4[C:10]([NH:11][C:2](=[O:30])[C:3]3=[N:16][N:17]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=4)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 312444-MethoxybenzaldehydeHCID 57470539HCID 57470539, compound

Product 1

HCID 58575390HCID 58575390, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 6.00 g of methyl 3-chloro-2-hydrazinoquinoxaline-6-carboxylate, 2.9 mL of 4-methoxybenzaldehyde, and 150 mL of acetic acid was stirred at room temperature for 3 hours. To the reaction mixture was added 4.74 g of copper(II) acetate, followed by stirring at 100° C. for 3 hours. Water was added thereto at room temperature, and the precipitated solid was collected by filtration and dried under reduced pressure. The obtained mixture was purified by silica gel column chromatography (chloroform/methanol) to obtain 5.27 g of methyl 1-(4-methoxyphenyl)-4-oxo-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate.

Workup

  1. stirringby stirring at 100° C. for 3 hours
  2. filtrationat room temperature, and the precipitated solid was collected by filtration
  3. customdried under reduced pressure
  4. customThe obtained mixture was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-3552527d88d54a2c842b36795f6577a8
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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