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

HRID 1388308ノート

反応式

HRID 1388308 の反応式
[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].C([OH:18])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:18])[CH2:6]1

参加物

3

反応物 2

HCID 702EthanolHCID 132689714-Acetyl-3-methyl-4-(4-pyridinyl)butanenitrile

生成物 1

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

実験手順

The same compound was prepared by the following procedure: Into a solution containing 81 g of 4-acetyl-3-methyl-4-(4-pyridinyl)butanenitrile dissolved in 250 ml of absolute ethanol was bubbled hydrogen chloride gas at ambient temperature with no cooling. After about 1 hour, a white solid began to crystallize. The reaction vessel was then stoppered and allowed to stand overnight at room temperature. The reaction mixture was evaporated to dryness in vacuo and the residue was dissolved in a small amount of water. The aqueous solution was made alkaline with concentrated ammonia hydroxide and the mixture was extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous magnesium sulfate, the mixture filtered and the filtrate evaporated in vacuo. The residue was slurried with acetonitrile and the solid, 5.4 g, was collected. This solid was combined with the product obtained as described in the immediately preceding paragraph along with the product obtained hereinbelow in Example C-3 and the combined material was recrystallized from about 250 ml of acetonitrile to yield 9.9 g of 3,4-dihydro-4,6-dimethyl-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. 186°-188° C.

後処理

  1. customThe same compound was prepared by the following procedure
  2. customwas bubbled hydrogen chloride gas at ambient temperature with no cooling
  3. customto crystallize
  4. waitto stand overnight at room temperature
  5. customThe reaction mixture was evaporated to dryness in vacuo
  6. dissolutionthe residue was dissolved in a small amount of water
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  9. filtrationthe mixture filtered
  10. customthe filtrate evaporated in vacuo
  11. customthe solid, 5.4 g, was collected
  12. customobtained
  13. customthe combined material was recrystallized from about 250 ml of acetonitrile

出典と根拠

ORDレコード
ord-ab2839cfc3a54836a176465560bff2d9
出典データセット
uspto-grants-1984_02
特許番号
US04431651

反応ノート

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