Water → 5-Chloro-6-hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 35675Notes

Reaction equation

HRID 35675 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7][CH2:6][C:5]2=[O:16].[Cl:17]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:17][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:16])[CH2:6][CH2:7][N:8]2[C:12](=[O:15])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 212948076-Hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 212947795-Chloro-6-hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinolineYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.643 g) and N-chlorosuccinimide (1.068 g) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 18 hours, poured into water, and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residual solid was recrystallized from chloroform to give 5-chloro-6-hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.74 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residual solid was recrystallized from chloroform

Sources & evidence

ORD record
ord-fa1b9d71ea7541dbb5c0c0561a49f4de
Source dataset
uspto-grants-1988_08
Patent number
US04767780

Reaction notes

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