Acetic Acid → HCID 19774980, compound

HRID 1073048Notes

Reaction equation

HRID 1073048 reaction equation
[CH3:1][NH:2][C:3]1CC(=O)[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=1.[C:15](OCC)(=[O:20])[CH2:16][C:17]([CH3:19])=O.[C:24]([OH:27])(=O)[CH3:25]>O>[CH3:19][C:17]1[C:25]2[C:24](=[O:27])[N:5]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:4][C:3]=2[N:2]([CH3:1])[C:15](=[O:20])[CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 178482486HCID 178482486, compound

Product 1

HCID 19774980HCID 19774980, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Methylamino-1-phenyl-2-pyrazolin-5-one (1.9 g), ethyl acetoacetate (1.4 g) and acetic acid (8 ml) were refluxed while stirring for 6 hours. The reaction solution was diluted with water, and the resulting crystals were collected by filtration and washed with isopropyl alcohol to obtain 1.8 g of 4,7-dimethyl-2-phenylpyrazolo(3,4-b)pyridine-3,6-dione (melting point 179 - 181oC). In a solution of these crystals (1 g) in methanol (20 ml) and triethylamine (0.7 ml), 1,7-diphenyl-1,7-diaza-1,3,5-heptatriene hydrochloride (0.7 g) was dissolved, and then acetic anhydride (0.6 ml) was added, and the mixture was 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]-4,7-dimethyl-2-phenylpyrazolo(3,4-b)pyridine-3, 6-dione (0.2 g). To these crystals (0.15 g), N,N-dimethylformamide (5 ml) and 4,7-dimethyl-2-phenylpyrazolo-(3,4-b)pyridine-3,6-dione (0.08 g) were added, and stirred at 50° C. for 2 hours. After filtration of the reaction solution, the filtrate was diluted with water for crystallization. The resulting crystals were collected by filtration, washed with water and dried to obtain compound II-1 (0.2 g). Melting point 300° C. or more, λmaxMeOH 760 nm.

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washwashed with isopropyl alcohol

Sources & evidence

ORD record
ord-f2608868f2084c6f9fad30a4acdefe23
Source dataset
uspto-grants-1990_11
Patent number
US04968593

Reaction notes

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