Hydrochloric Acid → 5-Amino-3-tert-butyl-1-(2-methylpyridine-5-yl)pyrazole

HRID 895943Notes

Reaction equation

HRID 895943 reaction equation
[NH:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1)[NH2:2].[CH3:10][C:11]([CH3:18])([CH3:17])[C:12](=O)[CH2:13][C:14]#[N:15].Cl.C(=O)([O-])O.[Na+]>CCO>[NH2:15][C:14]1[N:1]([C:3]2[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=2)[N:2]=[C:12]([C:11]([CH3:18])([CH3:17])[CH3:10])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 516892Sodium BicarbonateHCID 221471375-Hydrazinyl-2-methylpyridine

Product 1

HCID 114019745-Amino-3-tert-butyl-1-(2-methylpyridine-5-yl)pyrazoleYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-hydrazino-2-methyl-pyridine (8.0 g, 65.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (10.0 g, 79.9 mmol) in EtOH (200 mL) containing 6 N HCl (6 mL) was refluxed for 17 h, then cooled to room temperature. Solid sodium hydrogen carbonate was added to neutralize the solution. The slurry was filtered. The filtrate was concentrated. Column chromatography (silica gel, 2.5″×5″, eluant=EtOAc) afforded the desired 5-amino-3-tert-butyl-1-(2-methylpyridine-5-yl)pyrazole (9.21 g, 62%) as a tan solid.

Workup

  1. temperaturewas refluxed for 17 h
  2. filtrationThe slurry was filtered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8aea38d522bc428da5ec9d6560646da6
Source dataset
uspto-grants-2005_07
Patent number
US06916814B2

Reaction notes

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