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

HRID 35678노트

반응식

HRID 35678 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f23f40b0dd0349aab1fee5076710bd0b
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767780

반응 노트

불러오는 중…