Acetic Acid → 2,4'-Bipyridine

HRID 2241099Notes

Reaction equation

HRID 2241099 reaction equation
CO[CH:3](OC)[CH2:4][CH:5](OC)OC.[C:12]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)(=O)[CH3:13].C(O)(=O)C.C([O-])(=O)C.[NH4+:29].[OH-].[Na+]>CC(O)C>[N:29]1[CH:5]=[CH:4][CH:3]=[CH:13][C:12]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 142824-AcetylpyridineHCID 14798Sodium HydroxideHCID 66019TetramethoxypropaneHCID 517165Ammonium Acetate

Product 1

HCID 684882,4'-BipyridineYield 27.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

14.2 g (87 mmol) of 1,1,3,3-tetramethoxypropane, 10 g (83 mmol) of 4-acetylpyridine, 30 ml (500 mmol) of acetic acid and 39 g (500 mmol) of ammonium acetate were dissolved in 160 ml of 2-propanol, and the reaction solution was allowed to undergo the reaction at 80° C. for 9 hours. After completion of the reaction, this was cooled to room temperature, neutralized with 200 g (1.2 mol) of 25% sodium hydroxide aqueous solution and then extracted three times with 200 ml of toluene. The organic layer was concentrated and then purified by distillation under a reduced pressure to obtain 3.2 g (yield 27.6%) of the title compound (purity 98.2%).

Workup

  1. customthe reaction at 80° C. for 9 hours
  2. customAfter completion of the reaction
  3. extractionextracted three times with 200 ml of toluene
  4. concentrationThe organic layer was concentrated
  5. distillationpurified by distillation under a reduced pressure

Sources & evidence

ORD record
ord-3a971e812eda4bd2a34ac94da18abe4a
Source dataset
uspto-grants-2010_05
Patent number
US07723522B2

Reaction notes

Loading…