Hydrazine → 5-Fluoro-2-hydrazinylpyridine hydrofluoride

HRID 1948540Notes

Reaction equation

HRID 1948540 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[NH2:9][NH2:10]>>[FH:1].[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:9][NH2:10])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 27628712,5-Difluoropyridine

Product 1

HCID 717213885-Fluoro-2-hydrazinylpyridine hydrofluorideYield 45.3%

Conditions

Temperature
120 °C

Procedure

To 2,5-difluoropyridine (3 g, 26.1 mmol) was added hydrazine (1.636 ml, 52.1 mmol) and the contents were heated in a microwave at 120° C. for 1 h. Upon cooling, a white solid formed. The solid was collected by filtration, washed with ether and dried in vacuo to give 1.74 g of 5-fluoro-2-hydrazinylpyridine, hydrofluoride that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (1H, d, J=2.86 Hz), 7.42 (1H, td, J=8.80, 2.86 Hz), 7.35 (1H, br. s.), 6.73 (1H, dd, J=9.02, 3.74 Hz), 4.12 (2H, br. s.).

Workup

  1. temperatureUpon cooling
  2. customa white solid formed
  3. filtrationThe solid was collected by filtration
  4. washwashed with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c3f088dd26e14293825a9384803b5998
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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