Hydrazine → 5-Chloro-3-fluoro-2-hydrazinylpyridine

HRID 2176700Notes

Reaction equation

HRID 2176700 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:9])[C:5](F)=[N:6][CH:7]=1.[NH2:10][NH2:11]>CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([F:9])[C:5]([NH:10][NH2:11])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 27832485-Chloro-2,3-difluoropyridine

Product 1

HCID 226196745-Chloro-3-fluoro-2-hydrazinylpyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
67.5 °C

Procedure

A mixture of 5-chloro-2,3-difluoropyridine (10.0 g, 66.9 mmol) and hydrazine (10.0 ml, 319 mmol) in iPrOH (50 mL) was heated to 65-70° C. for 6 hours. The mixture was cooled to 23° C., filtered, and washed with Na2CO3 (satd), and H2O. Product isolated as a white solid. MS (ESI pos. ion) m/z: 162 (MH+). Calc'd exact mass for C5H5ClFN3: 161.

Workup

  1. temperatureThe mixture was cooled to 23° C.
  2. filtrationfiltered
  3. washwashed with Na2CO3 (satd), and H2O
  4. customProduct isolated as a white solid

Sources & evidence

ORD record
ord-5e7f9f73775b4885b69e83adc24e10b1
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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