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

HRID 1900566Notes

Reaction equation

HRID 1900566 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-0abaf9f445164fb2b41755c12273d21d
Source dataset
uspto-grants-1996_11
Patent number
US05576315

Reaction notes

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