Methylhydrazine → 3-tert-Butyl-1-methyl-1H-pyrazol-5-amine

HRID 479258Notes

Reaction equation

HRID 479258 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[CH3:10][NH:11][NH2:12]>C(O)CC>[NH2:6][C:5]1[N:11]([CH3:10])[N:12]=[C:3]([C:2]([CH3:9])([CH3:8])[CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 27352873-tert-Butyl-1-methyl-1H-pyrazol-5-amineYield 65.3%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of 12.5 g (0.1 mol) of 4,4-dimethyl-3-oxopentanenitrile in 50 cm3 of n-propanol were added, at room temperature, 4.6 g (0.1 mol) of methylhydrazine. The reaction medium was maintained at reflux for 1 hour and then cooled to room temperature. The white solid obtained was filtered off on a sinter funnel and then washed with isopropyl ether. After drying under vacuum at 40° C., 10 g of the expected product were obtained in the form of a beige solid, the melting point of which was 157° C.

Workup

  1. temperatureThe reaction medium was maintained
  2. temperatureat reflux for 1 hour
  3. customThe white solid obtained
  4. filtrationwas filtered off on a sinter funnel
  5. washwashed with isopropyl ether
  6. customAfter drying under vacuum at 40° C.

Sources & evidence

ORD record
ord-7fcb0b11ed2e4cd290fcef52925a68f6
Source dataset
uspto-grants-2003_11
Patent number
US06645258B2

Reaction notes

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