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

HRID 1756108Notes

Reaction equation

HRID 1756108 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.O.[NH2:10][NH2:11]>C(O)CC>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:10][NH2:11])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27828012-Chloro-5-fluoropyridine

Product 1

HCID 199167865-Fluoro-2-hydrazinylpyridineYield 122.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2-chloro-5-fluropyridine (5 g, 0.038 mol) and hydrazine monohydrate (15 ml, 0.32 mol) in n-propanol (40 ml) in a teflon container was purged with argon and heated in a stainless steel bomb at 200° C. for 19 h (magnetic stirring). Evaporation of solvent and excess hydrazine monohydrate in vacuo gave a solid residue (5.9 g) which was dissolved in sodium bicarbonate solution (5%) and extracted with 6×50 ml ethyl acetate. The combined extracts were dried over anhydrous Na2SO4, filtered and evaporated to give an oil (2.9 g) which proved difficult to purify and was therefore used as such in the next step. The crude product consisted of a ternary mixture of the desired product, 2-chloro-5-hydrazinopyridine, and 5-hydrazinopyridine.

Workup

  1. customwas purged with argon
  2. customEvaporation of solvent and excess hydrazine monohydrate in vacuo

Sources & evidence

ORD record
ord-abeb802833eb4a8cafd2c1c714729a40
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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