2-Hydrazinopyridine → ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate

HRID 497998Notes

Reaction equation

HRID 497998 reaction equation
C(O[CH:4]=[C:5]([C:11]#[N:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[NH2:14]>C(O)C>[NH2:12][C:11]1[N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:14]=[CH:4][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 742041ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(ethoxymethylene)-2-cyanoacetate (33.8 g, 200 mmol) and 2-hydrazinopyridine (21.8 g, 200 mmol) in ethanol (100 mL) was heated under reflux for 20 minutes. The solution was cooled to room temperature, and the resulting crystals were collected by filtration. The crystals were washed with ethanol and air dried to give the title compound (33.8 g, 73% yield).

Workup

  1. temperatureunder reflux for 20 minutes
  2. filtrationthe resulting crystals were collected by filtration
  3. washThe crystals were washed with ethanol and air
  4. customdried

Sources & evidence

ORD record
ord-ab24de07ac594ca78679be6901bbb08a
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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