Acetic Acid → 3-tert-butyl-1-phenyl-1H-pyrazol-5-amine

HRID 476555Notes

Reaction equation

HRID 476555 reaction equation
[C:1]([CH2:7][C:8]#[N:9])(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[C:10]1([NH:16][NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)C>C(O)C>[NH2:9][C:8]1[N:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:17]=[C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7516PhenylhydrazineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 7706343-tert-butyl-1-phenyl-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Pivaloyl acetonitrile (30.0 g; 0.24 mole) and ethanol (200 ml) were placed into a 500 ml round bottom flask. Phenylhydrazine (23.6 ml; 0.24 mole) was added with stirring followed by acetic acid (13.8 ml). The reaction was refluxed for 5 hours. Part of the ethanol was stripped off and the residue was poured into ice water. The product was filtered off and washed with water. The solid was dissolved in hot ethanol (100 ml), diluted with water, stirred, filtered, and washed with water. The yield of solid, m.p. 65°-7° C. was 46.3 g (90%).

Workup

  1. temperatureThe reaction was refluxed for 5 hours
  2. filtrationThe product was filtered off
  3. washwashed with water
  4. dissolutionThe solid was dissolved in hot ethanol (100 ml)
  5. additiondiluted with water
  6. stirringstirred
  7. filtrationfiltered
  8. washwashed with water

Sources & evidence

ORD record
ord-a4b5bc3cb66740678b49da862962aa8b
Source dataset
uspto-grants-1989_12
Patent number
US04885272

Reaction notes

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