Hydrazine hydrate (1:1) → N-benzyl-6-hydrazinylpyridine-3-carboxamide

HRID 578937

Reaction equation

HRID 578937 reaction equation
[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13](Cl)=[N:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:19][NH2:20]>C(O)C>[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH:19][NH2:20])=[N:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 857488N-Benzyl-6-chloro-nicotinamide

Product 1

HCID 51370238N-benzyl-6-hydrazinylpyridine-3-carboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combined N-benzyl-6-chloronicotinamide (13 g, 52.8 mmol) and ethanol (60 mL) then added hydrazine hydrate (85%, 30 mL) drop wise at room temperature. After the addition, the solution was heated to reflux overnight. The reaction mixture was then concentrated to remove ethanol and a solid was obtained. The solid was collected by filtration, washed with EtOAc (3×20 mL), and dried under reduced pressure to give the title compound (10 g, 78%) as an off-yellow solid.

Workup

  1. customwise at room temperature
  2. additionAfter the addition
  3. temperaturethe solution was heated
  4. temperatureto reflux overnight
  5. concentrationThe reaction mixture was then concentrated
  6. customto remove ethanol
  7. customa solid was obtained
  8. filtrationThe solid was collected by filtration
  9. washwashed with EtOAc (3×20 mL)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-9e0b4bbe7c7141d8a4a273bca2ec21fb
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Linked notes

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