Hydrazine hydrate (1:1) → 5-Chloro-2-hydrazinylpyridine

HRID 1289855Notes

Reaction equation

HRID 1289855 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.O.[NH2:10][NH2:11]>CCOCC>[NH:10]([C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1)[NH2:11]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 276852,5-Dichloropyridine

Product 1

HCID 135904645-Chloro-2-hydrazinylpyridineYield 82.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2,5-dichloropyridine (7.4 g, 50 mmol) and 50 ml of hydrazine hydrate (1 mol) was refluxed for 3 hours and the mixture was diluted with ether. The crystalline solid (1st crop) was filtered, the solid was washed with water; and the aqueous layer was extracted with ether (2×). The organic layer was partially concentrated in vacuo and filtered to yield an additional white solid (2nd crop). The concentration of the filtrate yielded more solid (third crop). The combined solid product was dried in vacuo to afford 5.95 g (82%) of 2-hydrazino-5-chloropyridine as a white solid, m.p. 116°-122° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationThe crystalline solid (1st crop) was filtered
  3. washthe solid was washed with water
  4. extractionand the aqueous layer was extracted with ether (2×)
  5. concentrationThe organic layer was partially concentrated in vacuo
  6. filtrationfiltered
  7. customto yield an additional white solid (2nd crop)
  8. customThe concentration of the filtrate yielded more solid (third crop)
  9. customThe combined solid product was dried in vacuo

Sources & evidence

ORD record
ord-8cb82b95dfbe4105bd1b826cf100fe67
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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