Sulfuric Acid → 2,4-Dimethyl-4,5-dihydro[3,4'-bipyridin]-6(1H)-one

HRID 1388307Notes

Reaction equation

HRID 1388307 reaction equation
[C:1]([CH:4]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[CH:5]([CH3:9])[CH2:6][C:7]#[N:8])(=O)[CH3:2].S(=O)(=O)(O)[OH:17]>C(O)(=O)C>[CH3:9][CH:5]1[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:1]([CH3:2])[NH:8][C:7](=[O:17])[CH2:6]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 132689714-Acetyl-3-methyl-4-(4-pyridinyl)butanenitrile

Product 1

HCID 132689722,4-Dimethyl-4,5-dihydro[3,4'-bipyridin]-6(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 2.0 g portion of 4-acetyl-3-methyl-4-(4-pyridinyl)butanenitrile dissolved in 20 ml of acetic acid was added dropwise 3 ml of sulfuric acid whereupon an exothermic reaction ensued. The reaction mixture was stirred for 4 hours, the acetic acid was evaporated off in vacuo and to the remaining material was added 10 ml of water followed by basification with 35% aqueous sodium hydroxide solution. The alkaline solution was extracted four times with ethyl acetate; the combined extracts were dried over anhydrous magnesium sulfate; the ethyl acetate was distilled off in vacuo; and, the remaining white solid was recrystallized from acetonitrile to produce 2.0 g of 3,4-dihydro-4,6-dimethyl-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 184°-186° C.

Workup

  1. customwhereupon an exothermic reaction
  2. customthe acetic acid was evaporated off in vacuo and to the remaining material
  3. additionwas added 10 ml of water
  4. extractionThe alkaline solution was extracted four times with ethyl acetate
  5. dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
  6. distillationthe ethyl acetate was distilled off in vacuo
  7. customand, the remaining white solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-93e400e519c24881b0c6065f83559ef3
Source dataset
uspto-grants-1984_02
Patent number
US04431651

Reaction notes

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