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

HRID 1250415Notes

Reaction equation

HRID 1250415 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-cd6d854813f342dc8267992ce5c27db5
Source dataset
uspto-grants-2002_01
Patent number
US06338741B1

Reaction notes

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