3-Ethoxy-2-propenenitrile → HCID 13007948, compound

HRID 1827630Notes

Reaction equation

HRID 1827630 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].C(O[CH:12]=[CH:13][C:14]#[N:15])C>C(O)CCCC>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[N:1]1[C:14]([NH2:15])=[CH:13][CH:12]=[N:2]1

Participants

4

Reactant 2

HCID 436013-Ethoxy-2-propenenitrileHCID 786452-Hydrazinopyridine2×

Product 1

HCID 13007948HCID 13007948, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A solution of 2-hydrazinopyridine (38.9 g, 453 mmol) was slowly added to a solution of 3-ethoxyacrylonitrile (31.5 g, 324 mmol) in pentanol (155 ml). The reaction mixture was brought to reflux for 5 h. 2-Hydrazinopyridine (10.6 g, 97 mmol) was again added and the reaction was allowed to continue to reflux for 4 h. The progress of the reaction is observed by TLC and, when the reaction is complete, the mixture is concentrated under reduced pressure until the excess hydrazinopyridine has precipitated. The filtrate was purified by column chromatography to give 2-pyridin-2-yl-2H-pyrazol-3-ylamine in the form of a white solid (2.75 g, 5.3%).

Workup

  1. temperatureto reflux for 5 h
  2. temperatureto reflux for 4 h
  3. concentrationthe mixture is concentrated under reduced pressure until the excess hydrazinopyridine
  4. customhas precipitated
  5. customThe filtrate was purified by column chromatography

Sources & evidence

ORD record
ord-c275d2d2912d488dbea11a462a090235
Source dataset
uspto-grants-2006_06
Patent number
US07056354B2

Reaction notes

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