Hydrazine hydrate (1:1) → HCID 67213134, compound

HRID 2108379Notes

Reaction equation

HRID 2108379 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[CH:8]=1)[C:5]#[N:6].O.[NH2:16]N>C(O)C>[CH3:13][C:9]1[CH:8]=[C:7]([C:4]2[CH:5]=[N:6][NH:2][C:3]=2[NH2:16])[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86598651α-[(Dimethylamino)methylene]-2-methyl-4-pyridineacetonitrile

Product 1

HCID 67213134HCID 67213134, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To stirred solution of 3-dimethylamino-2-(2-methyl-pyridin-4-yl)-acrylonitrile (1.8 g, 9.61 mmol) in ethanol (18 ml) was added at room temperature hydrazine monohydrate (1.03 ml, 21.1 mmol), the reaction mixture was heated under reflux conditions for 16 h and evaporated. Purification by column chromatography on silica gel (dichloromethane/methanol/NH4OH 80:10:1) and crystallization from diethyl ether yielded 4-(2-methyl-pyridin-4-yl)-2H-pyrazol-3-ylamine (0.6 g, 36%) as an orange solid.

Workup

  1. temperaturethe reaction mixture was heated under reflux conditions for 16 h
  2. customevaporated
  3. customPurification by column chromatography
  4. customon silica gel (dichloromethane/methanol/NH4OH 80:10:1) and crystallization from diethyl ether

Sources & evidence

ORD record
ord-5357ed3296c44b5aae8147a8f0853e48
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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