Hydrazine → 3,5-Dichloro-2-hydrazinylpyridine

HRID 453070

Reaction equation

HRID 453070 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][NH2:11]>O1CCOCC1>[Cl:8][C:7]1[C:2]([NH:10][NH2:11])=[N:3][CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 27666Pyridine, 2,3,5-trichloro-

Product 1

HCID 6009663,5-Dichloro-2-hydrazinylpyridineYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 500 mL flask, 2,3,5-trichloropyridine (20.00 g, 0.110 mol), 80% hydrazine (34.30 g, 0.550 mol) and dioxane (200 mL) were added sequentially. The reaction mixture was heated to reflux for 20 hours. Then the reaction mixture was cooled down to room temperature overnight and white crystal was precipitated. The white crystal was isolated via filtration and dried to give the product (14.0 g) as a white solid in 72% yield. Melting point: 187-189° C. 1H NMR (300 MHz, DMSO-d6): 8.123 (d, 1H), 7.849 (d, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 20 hours
  3. customwhite crystal was precipitated
  4. customThe white crystal was isolated via filtration
  5. customdried

Sources & evidence

ORD record
ord-77228aae130a4fbbaf2bddb21c1687bb
Source dataset
uspto-grants-2013_07
Patent number
US08492409B2

Linked notes

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