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

HRID 34511

Reaction equation

HRID 34511 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5](=[CH:8]OCC)[C:6]#[N:7])[CH3:2].[NH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[NH2:14]>C(O)C>[NH2:7][C:6]1[N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:14]=[CH:8][C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:12]

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-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl(ethoxymethylene)cyanoacetate, 19.5 g, was added in one portion into a solution of 2-hydrazinopyridine, 12.5 g, in 100 mL of absolute ethanol. The reaction was then heated at reflux for 21/2 hours and cooled. The solid which formed was collected by filtration and washed with absolute ethanol. After air-drying, the product weighed 22.6 g and melted at 92°-93° C.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for 21/2 hours
  3. temperaturecooled
  4. customThe solid which formed
  5. filtrationwas collected by filtration
  6. washwashed with absolute ethanol
  7. customAfter air-drying

Sources & evidence

ORD record
ord-411766317f3e45ec88ee92981df8d39a
Source dataset
uspto-grants-1988_08
Patent number
US04762550

Linked notes

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