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

HRID 1360407Notes

Reaction equation

HRID 1360407 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-5065ce42aaab450d84aa5c6470bb1b81
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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