4-Acetylpyridine → 5-nitro-2,4'-bipyridine

HRID 1594384Notes

Reaction equation

HRID 1594384 reaction equation
C[N:2](C)[CH:3]=[C:4]([N+:7]([O-:9])=[O:8])[CH:5]=O.[C:11]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)(=O)[CH3:12].CC(C)([O-])C.[K+].C([O-])(=O)C.[NH4+]>O1CCCC1.C(O)(=O)C>[N+:7]([C:4]1[CH:5]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[N:2][CH:3]=1)([O-:9])=[O:8]

Participants

7

Reactant 4

HCID 142824-AcetylpyridineHCID 517165Ammonium AcetateHCID 23665647Potassium tert-butoxideHCID 714437013-(Dimethylamino)-2-nitroprop-2-enal

Product 1

HCID 111832665-nitro-2,4'-bipyridineYield 72%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-(Dimethylamino)-2-nitro-2-propenal (60.5 g) was dissolved in tetrahydrofuran (500 ml). To the resulting solution were added 4-acetylpyridine (48.5 g) and potassium t-butoxide (121.14 g), for agitation at 30° C. for 30 minutes. After ammonium acetate (185 g) and acetic acid (140 ml) were added, reaction was progressed at an inner temperature of 95° C. for 4 hours while tetrahydrofuran was distilled off. To the reaction solution was added aqueous 25% NaOH solution (400 ml), for crystallization. The resulting crystal was dried to obtain the object compound in pale dark brown crystal (58 g; yield of 72%).

Workup

  1. customreaction
  2. distillationwas distilled off
  3. additionTo the reaction solution was added aqueous 25% NaOH solution (400 ml)
  4. customfor crystallization
  5. customThe resulting crystal was dried
  6. customto obtain the object compound in pale dark brown crystal (58 g; yield of 72%)

Sources & evidence

ORD record
ord-cb140ac129274265b68419caaa2c8369
Source dataset
uspto-grants-2007_11
Patent number
US07301029B2

Reaction notes

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