Hydrazine hydrate (1:1) → 3-Amino-5-phenylpyrazole

HRID 654593Notes

Reaction equation

HRID 654593 reaction equation
[C:1]([CH2:9][C:10]#[N:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:13][NH2:14]>C(O)C>[NH2:11][C:10]1[CH:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:14][N:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 64799Benzoylacetonitrile

Product 1

HCID 1366553-Amino-5-phenylpyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzoyl acetonitrile from part A hereinabove (10.0 g, 68.9 mmole) and hydrazine monohydrate (4.34 mL, 89.6 mmole) were combined in 95% ethanol (90 mL) and refluxed for 1.5 hours. The solvent was evaporated under vacuum and the crystalline subtitled compound, residue was crystallized from chloroform (three crops, 9.49 g, 86%, m.p. 125°-126.5°, lit., m.p. 123°-125°, Taylor, E. C. et al., J. Org. Chem., (1966), 31, page 1818.

Workup

  1. temperaturerefluxed for 1.5 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crystalline subtitled compound, residue was crystallized from chloroform (three crops, 9.49 g, 86%, m.p. 125°-126.5°, lit., m.p. 123°-125°, Taylor, E

Sources & evidence

ORD record
ord-35468fdf2cd145dab914074238851835
Source dataset
uspto-grants-1992_07
Patent number
US05132424

Reaction notes

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