Hydrochloric Acid → 4,7-dihydro-1,6-dimethyl-3-phenyl-4-(2-methylphenyl)-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid ethyl ester, hydrochloride

HRID 1031525

Reaktionsgleichung

Reaktionsgleichung von HRID 1031525
[CH2:1]([O:3][C:4](=[O:17])[C:5](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])[C:6]([CH3:8])=O)[CH3:2].[CH3:18][N:19]1[C:23]([NH2:24])=[CH:22][C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:20]1.[ClH:31].CO>C(O)C>[ClH:31].[CH2:1]([O:3][C:4]([C:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[C:22]2[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:20][N:19]([CH3:18])[C:23]=2[NH:24][C:6]=1[CH3:8])=[O:17])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5177791-Methyl-3-phenyl-1H-pyrazol-5-amineHCID 54239661Ethyl-2-(2-methylbenzyliden)acetoacetate2×

Produkt 1

HCID 1372254604,7-dihydro-1,6-dimethyl-3-phenyl-4-(2-methylphenyl)-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid ethyl ester, hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl-2-(2-methylbenzyliden)acetoacetate (0.050 mol) is added to 1-methyl-3-phenyl-5-pyrazolamine (0.050 mol) in ethanol (50 ml) and refluxed for 90 minutes. The mixture is then cooled to room temperature, further ethyl-2-(2-methylbenzyliden)acetoacetate (0.050 mol) is added thereto, and the mixture refluxed for further 90 minutes. The reaction mixture is then cooled, the solvent is evaporated, and the residue is taken up in ethyl ether, collected by filtration, and dried. The product is dissolved in methanol and a mixture of hydrochloric acid and methanol (45 mmol of HCl) is added thereto. The product of the title precipitates by adding ethyl ether. M.p. 187° C. (dec.).

Aufarbeitung

  1. temperaturerefluxed for 90 minutes
  2. temperaturethe mixture refluxed for further 90 minutes
  3. temperatureThe reaction mixture is then cooled
  4. customthe solvent is evaporated
  5. filtrationcollected by filtration
  6. customdried
  7. dissolutionThe product is dissolved in methanol
  8. additionis added
  9. customThe product of the title precipitates
  10. additionby adding ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a78c6a8330e642d08d1e3b3b76774091
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954508

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