Hydrazine hydrate (1:1) → Tert-butyl 6-hydrazinylpyridine-3-carboxylate

HRID 1913183Notes

Reaction equation

HRID 1913183 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:4][CH:3]=1.O.[NH2:16][NH2:17]>C(O)C>[NH:16]([C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:4][CH:3]=1)[NH2:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11521348Tert-butyl 6-chloropyridine-3-carboxylate

Product 1

HCID 45089857Tert-butyl 6-hydrazinylpyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

18.0 g (84.2 mmol) of tert-butyl 6-chloropyridine-3-carboxylate are initially charged in 85 ml of ethanol. 42.2 g (842.0 mmol) of hydrazine hydrate are added, and the mixture is stirred at 100° C. for 2 h. The mixture is then concentrated, and the residue is taken up in a mixture of ethyl acetate and water. The phases are separated, and the organic phase is washed once with water and once with saturated sodium chloride solution, dried over magnesium sulfate and concentrated again. The residue is triturated with petroleum ether, and the solid formed is filtered off and dried under high vacuum.

Workup

  1. concentrationThe mixture is then concentrated
  2. additionthe residue is taken up in a mixture of ethyl acetate and water
  3. customThe phases are separated
  4. washthe organic phase is washed once with water and once with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated again
  7. customThe residue is triturated with petroleum ether
  8. customthe solid formed
  9. filtrationis filtered off
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-414f3b0fdf38488f9e140f7c9557fa4f
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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