Ammonium Hydroxide → 1-butyl-5-methyl-1H-pyrazole-3-carboxamide

HRID 1984331Notes

Reaction equation

HRID 1984331 reaction equation
[CH2:1]([N:5]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]([O:13]CC)=O)=[N:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[NH4+:17]>CO>[CH2:1]([N:5]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]([NH2:17])=[O:13])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 66958271ethyl 1-butyl-5-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 669589581-butyl-5-methyl-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 1-butyl-5-methyl-1H-pyrazole-3-carboxylate (18.1 g, 86.1 mmol) in methanol (25 mL) was treated with ammonium hydroxide (25 mL) according to a modification of the method described in Part D of Examples 1-4. At the end of the reaction, the methanol was removed under reduced pressure, and the remaining solution was cooled in a refrigerator. A precipitate formed, was isolated by filtration, and was washed with water. The solid (9 g) was recrystallized from hexane (300 mL) and ethyl acetate (30 mL), isolated by filtration, washed with hexane, and air-dried to provide 6.95 g of 1-butyl-5-methyl-1H-pyrazole-3-carboxamide as colorless plates, mp 113.5-114.5° C.

Workup

  1. customAt the end of the reaction
  2. customthe methanol was removed under reduced pressure
  3. temperaturethe remaining solution was cooled in a refrigerator
  4. customA precipitate formed
  5. customwas isolated by filtration
  6. washwas washed with water
  7. customThe solid (9 g) was recrystallized from hexane (300 mL) and ethyl acetate (30 mL)
  8. customisolated by filtration
  9. washwashed with hexane
  10. customair-dried

Sources & evidence

ORD record
ord-e4596f72e52b497ba1a6166ea3572a9c
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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