Methylhydrazine → HCID 67496656, compound

HRID 1628238Notes

Reaction equation

HRID 1628238 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH2:9][C:10]#[N:11])[CH:5]=[CH:4][N:3]=1.[CH3:13][NH:14][NH2:15]>CO>[CH3:13][N:14]1[C:10]([NH2:11])=[CH:9][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)=[N:15]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 67497550HCID 67497550, compound

Product 1

HCID 67496656HCID 67496656, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a 100 ml flask was added 3-(2-methylpyridin-4-yl)-3-oxopropanenitrile 16.1.C, (465 mg, 2.9 mmole), 10 ml of MeOH and methyl hydrazine (249 μl, 7.26 mmole). The reaction was stirred at 70° C. for 8 hours at which time the solvent was removed with a stream of nitrogen. The crude product was purified by using a silica gel column (eluting with 5% MeOH in DCM) to give of 1-methyl-3-(2-methylpyridin-4-yl)-1H-pyrazol-5-amine 16.1.D as a yellow film (317 mg 49% yield). (Note: converted to HCl salt).

Workup

  1. customwas removed with a stream of nitrogen
  2. customThe crude product was purified
  3. washa silica gel column (eluting with 5% MeOH in DCM)

Sources & evidence

ORD record
ord-e2e72e403a184ed893bb2630d63e361d
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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