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 1031525Notes

Reaction equation

HRID 1031525 reaction equation
[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]

Participants

6

Reactant 4

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

Product 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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-a78c6a8330e642d08d1e3b3b76774091
Source dataset
uspto-grants-1990_09
Patent number
US04954508

Reaction notes

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