Sodium Hydroxide → N-Ethyl-1,3,5-trimethyl-1H-pyrazol-4-amine

HRID 586559Notes

Reaction equation

HRID 586559 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([NH:10][C:11]1[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=1[CH3:16])(=O)[CH3:8].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O>[CH2:7]([NH:10][C:11]1[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=1[CH3:16])[CH3:8]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride3×HCID 22335537N-(1,3,5-trimethylpyrazol-4-yl)acetamide

Product 1

HCID 22335539N-Ethyl-1,3,5-trimethyl-1H-pyrazol-4-amineYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Under an atmosphere of nitrogen, lithium aluminum hydride, LAH, (4.3 g, 113.6 mmol) was added portionwise to a vigorously stirred solution of 4-acetamido-1,3,5-trimethyl-1H-pyrazole (9.5 g, 56.8 mmol) of step A. After stirring at ambient temperature for 2 hours, the mixture was heated at reflux for 1 hour and the excess LAH was decomposed by the careful addition of 4.3 mL of H2O, 4.3 mL of 1N NaOH, 12.9 mL of H2O and 54 g Na2SO4. The solids were filtered and the filtrate concentrated in vacuo to give 7.26 g of title compound as a brown oil (91% crude yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe solids were filtered
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-d56902827f2441df9af02ee7ca3ee780
Source dataset
uspto-grants-2005_08
Patent number
US06936630B2

Reaction notes

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