Hydrazine hydrate (1:1) → HCID 67213144, compound

HRID 2108380Notes

Reaction equation

HRID 2108380 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([CH3:14])[CH:8]=1)[C:5]#[N:6].O.[NH2:17]N>C(O)C>[CH3:13][C:11]1[CH:12]=[C:7]([C:4]2[CH:5]=[N:6][NH:2][C:3]=2[NH2:17])[CH:8]=[C:9]([CH3:14])[N:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86598652HCID 86598652, compound

Product 1

HCID 67213144HCID 67213144, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To stirred solution of 3-dimethylamino-2-(2,6-dimethyl-pyridin-4-yl)-acrylonitrile (2.2 g, 10.9 mmol) in ethanol (22 ml) was added at room temperature hydrazine monohydrate (1.17 ml, 24.1 mmol), the reaction mixture was heated under reflux conditions for 23 h and evaporated. Purification by column chromatography on silica gel (dichloromethane/methanol/NH4OH 80:10:1) and crystallization from diethyl ether yielded 4-(2,6-dimethyl-pyridin-4-yl)-2H-pyrazol-3-ylamine (0.8 g, 39%) as a light brown solid. MS (ISP) 189.3 [(M+H)+]; mp 222° C.

Workup

  1. temperaturethe reaction mixture was heated under reflux conditions for 23 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-af48e17aa97a490897ed0e4967535621
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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