Acetic Anhydride → N'-(5-Bromopyridin-2-yl)acetohydrazide

HRID 589206Notes

Reaction equation

HRID 589206 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][NH2:16])=[N:13][CH:14]=1>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][NH:16][C:5](=[O:7])[CH3:6])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 53217374N'-(5-Bromopyridin-2-yl)acetohydrazideYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (1.13 mL, 12.0 mmol) was added to a solution of 5-bromo-2-hydrazinylpyridine (1.90 g, 10.0 mmol) and TEA (2.09 mL, 15.0 mmol) in DCM (200 mL). After 16 hours, the reaction mixture was concentrated by rotoevaporation and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with water and brine, dried with Na2SO4, and the solvent was removed under vacuum. The resulting residue was triturated with DCM to afford the title compound as a white solid (1.86 g).

Workup

  1. concentrationthe reaction mixture was concentrated by rotoevaporation
  2. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried with Na2SO4
  5. customthe solvent was removed under vacuum
  6. customThe resulting residue was triturated with DCM

Sources & evidence

ORD record
ord-89d2081218ff414f9f4cf215a87d06c4
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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