N,N-Dimethylaniline → 4-Oxo-1-propionyl-6-propionyloxy-1,2,3,4-tetrahydroquinoline

HRID 35678ノート

反応式

HRID 35678 の反応式
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:12][CH2:11][C:10]2=[O:21].CN(C)C1C=CC=CC=1>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[O:21]=[C:10]1[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([O:6][C:1](=[O:4])[CH2:2][CH3:3])[CH:8]=2)[N:13]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:12][CH2:11]1

参加物

6

反応物 3

HCID 949N,N-DimethylanilineHCID 62324Propionyl chlorideHCID 212948076-Hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 212948094-Oxo-1-propionyl-6-propionyloxy-1,2,3,4-tetrahydroquinoline収率 110.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6212Chloroform溶媒2 回

実験手順

A solution of propionyl chloride (1.018 g) in chloroform (5 ml) was added dropwise to a solution of 6-hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.09 g), N,N-dimethylaniline (1.513 g), and 4-dimethylaminopyridine (0.061 g) in chloroform (20 ml) with stirring and ice cooling over a period of 10 minutes After being stirred overnight at ambient temperature, the mixture was evaporated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed successively with 5% hydrochloric acid, water, aqueous sodium bicarbonate, and water, dried over magnesium sulfate, and evaporated in vacuo to give an oil of 4-oxo-1-propionyl-6-propionyloxy-1,2,3,4-tetrahydroquinoline (1.51 g).

後処理

  1. stirringice cooling over a period of 10 minutes After being stirred overnight at ambient temperature
  2. customthe mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed successively with 5% hydrochloric acid, water, aqueous sodium bicarbonate, and water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-f23f40b0dd0349aab1fee5076710bd0b
出典データセット
uspto-grants-1988_08
特許番号
US04767780

反応ノート

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