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

HRID 542522ノート

反応式

HRID 542522 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-852699ee849e482aaf6c536ae62e03b0
出典データセット
uspto-grants-1987_04
特許番号
US04657915

反応ノート

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