Hydrazine hydrate (1:1) → 5-Cyano-6-methylidene-hydrazino-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester

HRID 27761Notes

Reaction equation

HRID 27761 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:7][C:8]=1[CH:9]=O)#[N:2].O.[NH2:23][NH2:24]>CO>[C:1]([C:3]1[C:8](=[CH2:9])[NH:7][C:6]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:4]=1[NH:23][NH2:24])#[N:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 867372165-Cyano-6-formyl-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester

Product 1

HCID 867372185-Cyano-6-methylidene-hydrazino-2-piperidinyl-3-pyridine-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. filtrationThe title compound is filtered off
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b6e368cd66f1452f94f6937ff6470f10
Source dataset
uspto-grants-1980_09
Patent number
US04223142

Reaction notes

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