Cyanoacetamide → 1,2-Dihydro-6-methyl-2-oxo-5-phenyl-3-pyridinecarbonitrile

HRID 1980333

反応式

HRID 1980333 の反応式
CN(C)[CH:3]=[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](=O)[CH3:6].[C:15]([CH2:17][C:18]([NH2:20])=[O:19])#[N:16].C[O-].[Na+].C(OCC)(=O)C>CO.O>[C:15]([C:17]1[C:18](=[O:19])[NH:20][C:5]([CH3:6])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]=1)#[N:16]

参加物

7

反応物 4

HCID 7898CyanoacetamideHCID 8857Ethyl AcetateHCID 14883693-Buten-2-one, 4-(dimethylamino)-3-phenyl-HCID 10942334Sodium Methoxide

生成物 1

HCID 202311,2-Dihydro-6-methyl-2-oxo-5-phenyl-3-pyridinecarbonitrile

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

実験手順

A mixture of 4-dimethylamino-3-phenyl-3-butene-2-one (14.1 grams) and cyanoacetamide (5.9 grams) in 100 ml methanol was added to sodium methoxide (7.9 grams) in 100 ml methanol. The mixture was refluxed for 18 hours and then the crude reaction was stripped and the residue dissolved in a small amount of hot water. Acidification to pH 6-7 gave a gum-like solid which was collected by filtration. Further acidification to a lower pH gave only an oil. Trituration of the gum with ethyl acetate and chilling resulted in an off-white solid which was identified by NMR as the desired product, yield 2.8 grams, m.p. 280°-290° C.

後処理

  1. temperatureThe mixture was refluxed for 18 hours
  2. customthe crude reaction
  3. customAcidification to pH 6-7 gave a gum-like solid which
  4. filtrationwas collected by filtration
  5. customFurther acidification to a lower pH gave only an oil
  6. customresulted in an off-white solid which

出典と根拠

ORDレコード
ord-3dbe249ec74b4f19be4cd54366c3d2af
出典データセット
uspto-grants-1985_04
特許番号
US04508722

関連ノート

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