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

HRID 1995631

반응식

HRID 1995631 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ac9ef9b7538d471e8226a7b9c029c0e4
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04405552

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