(Phenylmethyl)hydrazine → 1-benzyl-3-methyl-1H-pyrazol-5-amine

HRID 479257Notes

Reaction equation

HRID 479257 reaction equation
[NH2:1]/[C:2](/[CH3:6])=[CH:3]\[C:4]#[N:5].[CH2:7]([NH:14]N)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)CCCC>[NH2:5][C:4]1[N:14]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:1]=[C:2]([CH3:6])[CH:3]=1

Participants

4

Reactant 2

HCID 11157(Phenylmethyl)hydrazineHCID 5325263(2Z)-3-Amino-2-butenenitrile

Product 1

HCID 7691461-benzyl-3-methyl-1H-pyrazol-5-amineYield 45.4%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

To a solution of 16.4 g (0.2 mol) of 3-aminocrotononitrile in 100 cm3 of n-pentanol were added 26.9 g (0.22 mol) of benzylhydrazine and the mixture was then heated at reflux for 12 hours. The n-pentanol was subsequently distilled off under reduced pressure and a thick oil was obtained, which was purified by chromatography on silica gel. A pale yellow solid was obtained, which was crystallized from isopropyl ether and was then filtered on a sinter funnel. After drying under vacuum at 40° C., 17 g of the expected product were obtained in the form of a pale yellow solid, the melting point of which was from 76 to 78° C.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 12 hours
  3. distillationThe n-pentanol was subsequently distilled off under reduced pressure
  4. customa thick oil was obtained
  5. customwhich was purified by chromatography on silica gel
  6. customA pale yellow solid was obtained
  7. customwhich was crystallized from isopropyl ether
  8. filtrationwas then filtered on a sinter funnel
  9. customAfter drying under vacuum at 40° C.

Sources & evidence

ORD record
ord-366fcb022e80483c8bdf88ec40f17d1e
Source dataset
uspto-grants-2003_11
Patent number
US06645258B2

Reaction notes

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