Dimethylformamide → 2-[2-(Dimethylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitrile

HRID 542522노트

반응식

HRID 542522 반응식
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([C:10]#[N:11])=[CH:5][CH:4]=1.CO[C:14](OC)([N:16]([CH3:18])[CH3:17])[CH3:15].CN(C)C=O>CO>[CH3:17][N:16]([CH3:18])[C:14]([CH3:15])=[CH:9][C:7]1[C:6]([C:10]#[N:11])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 137499186-Methoxy-2-methylpyridine-3-carbonitrile

생성물 1

HCID 543079292-[2-(Dimethylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitrile

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
130 °C

실험 절차

A mixture containing 47.2 g of 6-methoxy-2-methyl-3-pyridinecarbonitrile, 100 ml of dimethylacetamide dimethyl acetal and 100 ml of dimethylformamide was heated with stirring in an oil bath at 130° C. for 1 hour and 45 minutes. The temperature of the oil bath was raised to 150° C. and the methanol formed by the reaction was distilled off using a 12" distillation column (Vigreux) while continuing the heating at 150° C. for 14 hours. The reaction mixture was concentrated, 50 ml of ether was added to the concentrated solution whereupon the product crystallized out. The mixture was chilled and the crystalline solid collected. The solid was washed with cold ether, dried and recrystallized from ethyl acetate using decolorizing charcoal to yield 33.5 g of 2-[2-(dimethylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitrile, m.p. 103°-104° C.

후처리

  1. temperaturewas heated
  2. temperatureThe temperature of the oil bath was raised to 150° C.
  3. distillationwas distilled off
  4. distillationa 12" distillation column (Vigreux)
  5. customheating at 150° C.
  6. customfor 14 hours
  7. concentrationThe reaction mixture was concentrated
  8. addition50 ml of ether was added to the concentrated solution whereupon the product
  9. customcrystallized out
  10. temperatureThe mixture was chilled
  11. customthe crystalline solid collected
  12. washThe solid was washed with cold ether
  13. customdried
  14. customrecrystallized from ethyl acetate using

출처 및 근거

ORD 기록
ord-852699ee849e482aaf6c536ae62e03b0
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04657915

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