Hydrazine hydrate (1:1) → (4-Hydroxymethyl-2,3,5-trifluoropyridin-6-yl)hydrazine

HRID 256157Notes

Reaction equation

HRID 256157 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([F:9])=[C:7](F)[N:6]=[C:5]([F:11])[C:4]=1[F:12].O.[NH2:14][NH2:15]>C(O)C>[OH:1][CH2:2][C:3]1[C:8]([F:9])=[C:7]([NH:14][NH2:15])[N:6]=[C:5]([F:11])[C:4]=1[F:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 139851584-Hydroxymethyl-2,3,5,6-tetrafluoropyridine

Product 1

HCID 13985160(4-Hydroxymethyl-2,3,5-trifluoropyridin-6-yl)hydrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.0 g (0.0055 mole) of 4-hydroxymethyl-2,3,5,6-tetrafluoropyridine (from Example 5) in 50 ml of ethanol was added 0.2 g (0.004 mole) of hydrazine hydrate. This mixture was stirred for approximately twenty-four hours during which a white precipitate formed. The reaction mixture was filtered, and the filtrate was concentrated by evaporating the solvent under reduced pressure. Water and ether were added to this residue. The ether layer was separated, dried, and the solvent evaporated, leaving a yellow solid, (4-hydroxymethyl-2,3,5-trifluoropyridin-6-yl)hydrazine. The structure and nmr data are set forth in Table 1C.

Workup

  1. customformed
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customby evaporating the solvent under reduced pressure
  5. additionWater and ether were added to this residue
  6. customThe ether layer was separated
  7. customdried
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-25a321ef0f42488e9da23e3b79057915
Source dataset
uspto-grants-1987_10
Patent number
US04701464

Reaction notes

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