Acetic Acid → HCID 22157904, compound

HRID 1073049Notes

Reaction equation

HRID 1073049 reaction equation
[C:1](OCC)(=[O:6])[CH2:2][C:3]([CH3:5])=O.C(O)(=O)C.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[CH2:27][C:26](=[O:28])[N:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:24]=2)=[CH:18][CH:17]=1.O>CO.CC(C)=O>[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[C:1](=[O:6])[CH:2]=[C:3]([CH3:5])[C:27]3[C:26](=[O:28])[N:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[NH:24][C:23]2=3)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8868Ethyl AcetoacetateHCID 178492218HCID 178492218, compound

Product 1

HCID 22157904HCID 22157904, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

Ethyl acetoacetate (8.5 g) and acetic acid (75 ml) were added to 3-(4-methoxyphenylamino)-1-phenyl-2-pyrazolin-5-one (14 g) and refluxed while heating for 6 hours. The reaction solution was poured into 150 ml of water, and the resulting solid was dissolved in a mixture of methanol (500 ml) and acetone (150 ml) while heating. The solution was cooled to obtain 8.4 g of 7-(4-methoxyphenyl)-4-methyl-2-phenylpyrazolo(3,4-b)pyridine-3,6-dione (melting point 189°-190° C.). In a solution prepared by adding methanol (40 ml) and triethylamine (2.8 ml) to these crystals (3.47 g) was dissolved, 1,7-diphenyl-1,7-diaza-1,3,5-heptatriene hydrochloride (2.85 g), and then acetic anhydride (1.88 ml) was added thereto, and stirred at room temperature for one hour. The resulting precipitate was collected by filtration, washed with methanol and dried to obtain 5-[5-(N-acetylanilino)-2,3-pentadienylidene]-7-(4-methoxyphenyl)-4-methyl-2-phenylpyrazolo(3,4-b)pyridine-3,6 -dione (4.1 g). N,N-dimethylformamide (40 ml), 7-(4-methoxyphenyl)-4-methyl-1-phenyl- 2-pyrazolin-5-one (2.4 g) and triethylamine (0.98 ml) were added to these crystals (3.8 g), and stirred at 50° C. for 2 hours. After filtration of the reaction solution, 10-fold volume of ethyl acetate was added for crystallization. The crystals were recrystallized from acetonitrile to obtain compound II-3 (1.0 g). Melting point 260° C. (decomposed).

Workup

  1. temperaturerefluxed
  2. temperaturewhile heating for 6 hours
  3. temperaturewhile heating
  4. temperatureThe solution was cooled

Sources & evidence

ORD record
ord-b5bfb3cebd57463a8bb8c5cfad14c575
Source dataset
uspto-grants-1990_11
Patent number
US04968593

Reaction notes

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