Water → 2-Hydrazinyl-5-nitropyridine

HRID 37448

Reaction equation

HRID 37448 reaction equation
O.[NH2:2][NH2:3].O.Cl[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][N:7]=1>C(O)C>[NH:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][N:7]=1)[NH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 783082-Chloro-5-nitropyridine

Product 1

HCID 40319312-Hydrazinyl-5-nitropyridineYield 77.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of hydrazine hydrate (30.0 equivalents), water (4 ml/gm of pyridine), and ethanol (2 ml/gm of pyridine) was added 2-chloro-5-nitropyridine (1 equivalent). The reaction mixture was stirred at 20° for 16 hours (a very thick green slurry forms). The precipitate was isolated by filtration and the solid was washed with methanol and then ether to give a green solid. The product was used without further purification; yield 77.3%; m.p. 205°-207°. IR {KBr): 3340, 3200, 2980, 1670, 1605, 1580, 1485, 1420, 1330, 1300, 1120, 980, 830, 770 cm-1.

Workup

  1. customThe precipitate was isolated by filtration
  2. washthe solid was washed with methanol
  3. customether to give a green solid
  4. customThe product was used without further purification

Sources & evidence

ORD record
ord-4c57f95f2e1b4fcc8dd9b527d8bf30de
Source dataset
uspto-grants-1995_05
Patent number
US05420285

Linked notes

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