Hydrazine hydrate (1:1) → 3-(2-Pyridyl)propanoic acid, hydrazide

HRID 128645Notes

Reaction equation

HRID 128645 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([O:11]CC)=O.O.[NH2:15][NH2:16]>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([NH:15][NH2:16])=[O:11]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 347337Ethyl 3-(pyridin-2-yl)propanoate

Product 1

HCID 149759843-(2-Pyridyl)propanoic acid, hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring 5 mL EtOH solution of 0.58 g (3.2 mmol) of ethyl 3-(2-pyridinyl)propanoate (4), prepared as described above in Example 4, was added 0.32 g (6.5 mmol) of hydrazine hydrate. The reaction was heated at reflux for three weeks. Although the reaction was still incomplete, the solvent was removed under vacuum. The resulting gum was triturated with diethyl ether (Et2O). The product remained a gum. The yield of 3-(2-pyridyl)propanoic acid, hydrazide (5) was 0.22 g (42%). This product was used immediately in the manner described in Example 6 below.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for three weeks
  3. customthe solvent was removed under vacuum
  4. customThe resulting gum was triturated with diethyl ether (Et2O)

Sources & evidence

ORD record
ord-9206fb88e4ec4095b8af184fdb14bb08
Source dataset
uspto-grants-1995_11
Patent number
US05464830

Reaction notes

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