HCID 135783976, compound → HCID 135783975, compound

HRID 1580977Notes

Reaction equation

HRID 1580977 reaction equation
[CH2:1]([N:3]1[C:7]2[NH:8][C:9](=[O:16])[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[C:6]=2[CH:5]=[N:4]1)[CH3:2].[H][H]>[Rh].C(O)C>[CH2:1]([N:3]1[C:7]2[NH:8][C:9](=[O:16])[CH2:10][CH:11]([C:12]([F:13])([F:15])[F:14])[C:6]=2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 135783976HCID 135783976, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135783975HCID 135783975, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

16.2 G. of 1-ethyl-1,7-dihydro-4-(trifluoromethyl)-6H-pyrazolo[3,4-b]pyridin-6-one, dissolved in 250 ml. of absolute ethanol, are catalytically hydrogenated by means of rhodium on charcoal catalyst (5%) at a temperature of 90°-100°. The reaction is performed in an autoclave at a hydrogen pressure of 10 atm. for 14 hours. After cooling, the catalyst is filtered off and the solution evaporated to dryness. The residual 1-ethyl-1,4,5,7-tetrahydro-4-(trifluoromethyl)-6H-pyrazolo[3,4-b]pyridin-6-one is treated with hot hexane providing 13.3 g. (81.5%) of the compound, m.p. 129°-130°. Recrystallization from a mixture of benzene/petroleum ether (1:2) raises the melting point at 130°-132°.

Workup

  1. temperatureAfter cooling
  2. filtrationthe catalyst is filtered off
  3. customthe solution evaporated to dryness
  4. additionThe residual 1-ethyl-1,4,5,7-tetrahydro-4-(trifluoromethyl)-6H-pyrazolo[3,4-b]pyridin-6-one is treated with hot hexane providing 13.3 g
  5. customRecrystallization
  6. additionfrom a mixture of benzene/petroleum ether (1:2)
  7. temperatureraises the melting point at 130°-132°

Sources & evidence

ORD record
ord-13d2d399b4e642488f1d4865a2e40316
Source dataset
uspto-grants-1976_01
Patent number
US03935222

Reaction notes

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