1-Butanol → 5-Fluoro-2-hydrazinylpyridine

HRID 1623990Notes

Reaction equation

HRID 1623990 reaction equation
O.[NH2:2][NH2:3].C(O)CCC.Cl[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][N:11]=1>CCO>[F:16][C:13]1[CH:14]=[CH:15][C:10]([NH:2][NH2:3])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 24654Hydrazine hydrate (1:1)HCID 27828012-Chloro-5-fluoropyridine

Product 1

HCID 199167865-Fluoro-2-hydrazinylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of hydrazine monohydrate (14.75 mL, 304 mmol) and 1-butanol (10 mL) was added 2-chloro-5-fluoropyridine (5.00 g, 38.0 mmol). The solution was microwaved in a sealed, thick-walled glass tube at 180° C. for 1 h. The resulting white suspension was transferred with EtOH to a round bottom flask then concentrated. The resulting white solid was taken up in ethyl acetate (250 mL) and the insoluble material removed by filtration. The filtrate was concentrated to give the title compound a pale orange solid. This solid was used in the following step without further purification.

Workup

  1. customThe solution was microwaved in a sealed, thick-walled glass tube at 180° C. for 1 h
  2. concentrationthen concentrated
  3. customthe insoluble material removed by filtration
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5e335dc36d0843df8cf524407bfd0ee7
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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