Hydrazine → N-benzyl-6-hydrazinylpyridine-3-carboxamide

HRID 578945Notes

Reaction equation

HRID 578945 reaction equation
[NH2:1][NH2:2].[CH2:3]([NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15](Cl)=[N:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([NH:1][NH2:2])=[N:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 857488N-Benzyl-6-chloro-nicotinamide

Product 1

HCID 51370238N-benzyl-6-hydrazinylpyridine-3-carboxamideYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combined hydrazine (1.67 mL, 53.3 mmol) and a solution of N-benzyl-6-chloronicotinamide (2.19 g, 8.88 mmol) in ethanol (70 mL) and heated overnight at 100° C. The reaction mixture was then cooled and evaporated to give a solid. The solid was collected by filtration, washed with 70 mL water, and recrystallized from hot ethanol to give the title compound (1.32 g, 61%) as an off-white solid. MS m/z [M+H]+ 243.2.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customevaporated
  3. customto give a solid
  4. filtrationThe solid was collected by filtration
  5. washwashed with 70 mL water
  6. customrecrystallized from hot ethanol

Sources & evidence

ORD record
ord-14b67b7531074a73bb6f79bf4d75ec0a
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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