Heptane → 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine hydrochloride

HRID 2308405Notes

Reaction equation

HRID 2308405 reaction equation
[C:1]([CH2:7][C:8]#[N:9])(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[ClH:10].[C:11]1([CH3:19])[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1.CCCCCCC>CO>[ClH:10].[NH2:9][C:8]1[N:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:19])=[CH:12][CH:13]=2)[N:18]=[C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:7]=1

Participants

5

Reactant 3

HCID 8900HeptaneHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 119912003-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of pivaloylacetonitrile (750 g, 6.0 mol) and p-tolylhydrazine hydrochloride (660 g, 4.2 mol) in methanol (2.8 L) was refluxed for 3 h. Heptane was added, and methanol was removed by distillation. The product was crystallized from the solution, collected by filtration and dried in vacuum oven to constant weight. Yield: 1.05 kg, 94%. 1H NMR δ (CDCl3) 7.50 (d, 2H), 7.30 (d, 2H), 5.60 (s, 1H), 2.45 (s, 3H), 1.40 (s, 9H). MS (CI) m/z 229 (M++H).

Workup

  1. custommethanol was removed by distillation
  2. customThe product was crystallized from the solution
  3. filtrationcollected by filtration
  4. customdried in vacuum oven to constant weight

Sources & evidence

ORD record
ord-cfe3b9e0fcf94364a1c909ad2c97da6f
Source dataset
uspto-grants-2004_12
Patent number
US06835832B2

Reaction notes

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