Hydrazine → Methyl 6-hydrazinylpyridine-3-carboxylate

HRID 338847Notes

Reaction equation

HRID 338847 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH2:12][NH2:13]>C1COCC1>[NH:12]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1)[NH2:13]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 13758765Methyl 6-fluoropyridine-3-carboxylate

Product 1

HCID 55280209Methyl 6-hydrazinylpyridine-3-carboxylateYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 6-fluoronicotinate (13.9 g, 89.60 mmol) and hydrazine (5.625 ml, 179.2 mmol) in THF (200 mL) were heated at 56° C. for 2 hours. After cooling to ambient temperature, the solvent was removed under reduced pressure and water (200 mL) was added. The suspension was stirred at ambient temperature for 1 hour. The solid was collected by filtration, washed with water and dried to give methyl 6-hydrazinylnicotinate (13.4 g, 89.5%) as a solid.

Workup

  1. customthe solvent was removed under reduced pressure and water (200 mL)
  2. additionwas added
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c937c3d86bc743d4970c90d94f93d68f
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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