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

HRID 653128Notes

Reaction equation

HRID 653128 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

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).

Workup

  1. stirringAfter 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

Sources & evidence

ORD record
ord-98a27ab94d814c4c9e57f9e58189de96
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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