Reaction #56039

ord-b6e368cd66f1452f94f6937ff6470f10

Reaction equation

CCOC(=O)c1cc(C#N)c(C=O)nc1N1CCCCC1
5-cyano-6-formyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester
NN.O
hydrazine hydrate
→
C=C1NC(N2CCCCC2)=C(C(=O)OCC)C(NN)=C1C#N
5-Cyano-6-methylidene-hydrazino-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester

Reactants

CCOC(=O)c1cc(C#N)c(C=O)nc1N1CCCCC1
5-cyano-6-formyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester
NN.O
hydrazine hydrate

Reagents

None

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe title compound is filtered off
  2. 2
    Otherrecrystallized from methanol

Procedure

28.7 g of 5-cyano-6-formyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester (0.1 mol) are dissolved in 100 ml of methanol. 5.5 g of hydrazine hydrate are added and the solution is stirred at room temperature over night. The title compound is filtered off and recrystallized from methanol. Yield 20.5 g (68%); m.p. 168°-170° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04223142uspto-grants-1980_09