Acetic Acid → 5(6H)-Quinolinone, 7,8-dihydro-

HRID 863009

反応式

HRID 863009 の反応式
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.C(O)(=O)C.[C:13]1(C)[CH:18]=CC=C[CH:14]=1>>[N:1]1[C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]=2[CH:18]=[CH:13][CH:14]=1

参加物

4

反応物 3

HCID 176Acetic AcidHCID 1140TolueneHCID 788923-Aminocyclohex-2-en-1-one

生成物 1

HCID 30168115(6H)-Quinolinone, 7,8-dihydro-

実験手順

A mixture of 57.93 g of 3-amino-2-cyclohexene-1-one, 76.8 g of 3-(dimethylamino)acrotein, 62.5 ml of glacial acetic acid and 270 ml of toluene is refluxed under argon for 16 hours and concentrated under vacuum to dryness. Toluene (200 ml) is added and the solvent removed under vacuum. To the residue is added one liter of dichloromethane and then 200 ml of saturated NaHCO3 slowly added and solid NaHCO3 added to bring the pH to 8. The mixture is filtered and the CH2Cl2 layer separated. The CH2Cl2 layer is passed through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residual black oil is extracted with hot hexane and the hexane decanted. This process is repeated until no more product extracted into the hexane. The hexane extracts are combined and the solvent removed to give 17.3 g of product as an oil.

後処理

  1. temperatureis refluxed under argon for 16 hours
  2. concentrationconcentrated under vacuum to dryness
  3. additionToluene (200 ml) is added
  4. customthe solvent removed under vacuum
  5. additionTo the residue is added one liter of dichloromethane
  6. addition200 ml of saturated NaHCO3 slowly added
  7. additionsolid NaHCO3 added
  8. filtrationThe mixture is filtered
  9. customthe CH2Cl2 layer separated
  10. concentrationthe filtrate concentrated to dryness
  11. extractionThe residual black oil is extracted with hot hexane
  12. customthe hexane decanted
  13. extractionextracted into the hexane
  14. customthe solvent removed

出典と根拠

ORDレコード
ord-afdee911fb524958bdb6a268acf7272b
出典データセット
uspto-grants-1998_02
特許番号
US05719278

関連ノート

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