Hydrazine → 1-(5-(5-Chloropyridin-2-yl)-3-fluoropyridin-2-yl)hydrazine

HRID 219278Notes

Reaction equation

HRID 219278 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([F:15])[C:11](F)=[N:12][CH:13]=2)=[N:6][CH:7]=1.[NH2:16][NH2:17]>CC(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([F:15])[C:11]([NH:16][NH2:17])=[N:12][CH:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 580155045-(5-Chloropyridin-2-yl)-2,3-difluoropyridine

Product 1

HCID 580155171-(5-(5-Chloropyridin-2-yl)-3-fluoropyridin-2-yl)hydrazineYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-(5-chloropyridin-2-yl)-2,3-difluoropyridine (2.4 g, 11 mmol) in IPA (35 mL, 0.3 M) at room temperature was added hydrazine (4 mL, 127 mmol). The reaction mixture was stirred at 60° C. for 2 h, at which point the reaction was cooled to room temperature and concentrated in vacuo. The concentrated material was suspended in saturated NaHCO3 and filtered to obtain product as a white, fluffy solid. The material was re-suspended in water (30 mL), and filtered to obtain 1-(5-(5-chloropyridin-2-yl)-3-fluoropyridin-2-yl)hydrazine (2.1 g, 83% yield). MS m/z=239.2 [M+1]+. Calc'd for C10H8ClFN4: 238.6.

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered
  4. customto obtain product as a white, fluffy solid
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d1d40b64455a430d8940776942971f1c
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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