Ethanol → HCID 19432749, compound

HRID 487243Notes

Reaction equation

HRID 487243 reaction equation
[OH-].[K+].[CH3:3][CH:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[N:9]1[C:13]([NH2:14])=[C:12]([C:15]#[N:16])[C:11]([CH3:17])=[N:10]1.OO.C([OH:22])C>O.CO>[CH3:3][CH:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[N:9]1[C:13]([NH2:14])=[C:12]([C:15]([NH2:16])=[O:22])[C:11]([CH3:17])=[N:10]1

Participants

7

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 19432763HCID 19432763, compound

Product 1

HCID 19432749HCID 19432749, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

85% Potassium hydroxide (5.8 g, 88.5 mmol) was dissolved in water (50 ml) and the solution was cooled in an ice bath for 1 hour. The 1-(2-methylcyclopentyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile (2.6 g, 12.7 mmol) in methanol (5.0 ml)/water (25 ml) was then added, followed by 30% hydrogen peroxide (6.5 ml, 63.2 mmol). The reaction mixture was stirred with ice-bath cooling for 4 hours, then was warmed slowly to room temperature. Ethanol was added to the reaction mixture to completely dissolve the starting material and the mixture was stirred at room temperature for 60 hours. The ethanol was removed in vacuo and the oily residue was extracted with ethyl acetate (3×100 ml). The combined organic layers were dried over anhydrous MgSO4 and the solvents were removed in vacuo to afford an amber solid. Recrystallization from acetonitrile and air drying then afforded 2.4 g (84%) of 1-(2-methylcyclopentyl)-3-methyl-5-amino- 1H-pyrazole-4-carboxamide as an off-white solid, m.p. 124°-126° C.

Workup

  1. temperaturethe solution was cooled in an ice bath for 1 hour
  2. temperaturecooling for 4 hours
  3. dissolutionto completely dissolve the starting material
  4. stirringthe mixture was stirred at room temperature for 60 hours
  5. customThe ethanol was removed in vacuo
  6. extractionthe oily residue was extracted with ethyl acetate (3×100 ml)
  7. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  8. customthe solvents were removed in vacuo
  9. customto afford an amber solid
  10. customRecrystallization from acetonitrile and air
  11. customdrying

Sources & evidence

ORD record
ord-2e3e52e3904340e98a386219d41240de
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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