Hydrazine → Picolinohydrazide

HRID 1982385Notes

Reaction equation

HRID 1982385 reaction equation
[NH2:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([O:11]CC)=O>C(O)C>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([NH:1][NH2:2])=[O:11]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 17307Ethyl 2-pyridinecarboxylate2×

Product 1

HCID 255881Picolinohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyridine-2-carboxylic acid hydrazide is prepared as follows: 230 g (228 mL) of anhydrous hydrazine is added, over a period of 10-15 minutes, to a stirred solution of 977.4 g of ethyl pyridine-2-carboxylate ((ethyl picolinate) in 1750 mL of anhydrous ethanol. The reaction is exothermic. The solution is stirred and refluxed for 5 hours, then stirred at room temperature overnight. The crystalline product is filtered off, washed first with anhydrous alcohol and then with anhydrous ether, and air-dried to yield pyridine-2-carboxylic acid hydrazide, m.p. 95°-100°.

Workup

  1. customPyridine-2-carboxylic acid hydrazide is prepared
  2. temperaturerefluxed for 5 hours
  3. stirringstirred at room temperature overnight
  4. filtrationThe crystalline product is filtered off
  5. washwashed first with anhydrous alcohol
  6. dry with materialwith anhydrous ether, and air-dried

Sources & evidence

ORD record
ord-73d0de66f4fd4a899143572f8e8a5042
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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