Sodium Hydroxide → 1-tert-Butyl-3-phenyl-1H-pyrazol-5-amine

HRID 1594026Notes

Reaction equation

HRID 1594026 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].O=[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][C:13]#[N:14]>CCO>[C:2]([N:6]1[C:13]([NH2:14])=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:7]1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 64799BenzoylacetonitrileHCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 119912031-tert-Butyl-3-phenyl-1H-pyrazol-5-amineYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry of tert-butylhydrazine hydrochloride (12.8 g, 102.9 mmol) in 350 mL of EtOH was added sodium hydroxide (3.5 g, 88.2 mmol). After 1 hr of stirring, a solution of 3-oxo-3-phenyl-propionitrile (10.6 g, 73.5 mmol, in 50 mL of EtOH) was added and the resulting slurry was heated to reflux. After 12 hr, the reaction was cooled to room temperature, filtered, and concentrated under reduced pressure. The resulting solid was washed with hexanes and dried under reduced pressure to give the title compound (13.1 g, 83% yield) as yellow-colored solid, which was used without further purification. LRMS m/z /(APCl) 216 (M+1); 500 MHz 1H NMR (CD3OD) δ 7.67 (d, J=7.5 Hz, 2H), 7.35-7.29 (m, 2H), 7.25-7.20 (m, 1H), 5.86 (s, 1H), 1.65 (S, 9H).

Workup

  1. temperaturethe resulting slurry was heated to reflux
  2. waitAfter 12 hr
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting solid was washed with hexanes
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4e4f31f03e5b44398570ab7990d3e80e
Source dataset
uspto-grants-2007_11
Patent number
US07300943B2

Reaction notes

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