Water → HCID 21533403, compound

HRID 1657449Notes

Reaction equation

HRID 1657449 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH:10]=2)([O:3][CH2:4][CH3:5])=[O:2].[H-].[Na+].O.[CH2:26](I)[CH3:27]>CN(C)C=O>[CH2:26]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:10]=2)[C:15](=[O:16])[C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:7]1)[CH3:27]

Participants

6

Reactant 4

HCID 962Water2×HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178469488HCID 178469488, compound

Product 1

HCID 21533403HCID 21533403, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 32.7 g of 3 -carboethoxy-4-hydroxy-7-cyclohexyl-quinoline and 7.1 g of sodium hydride (50% strength in mineral oil) in 400 ml of absolute dimethylformamide is stirred for 45 minutes at room temperature with exclusion of water. In the course thereof, the temperature of the reaction mixture rises to 35°C and a homogeneous solution is produced. 39 g of ethyl iodide are added dropwise to this solution over the course of 10 minutes whilst stirring and the mixture is stirred for a further 21/2hours at 55°C. It is then cooled to room temperature and 500 ml of water are added slowly, whilst stirring. The resulting precipitate is filtered off, well washed with water and recrystallised from ethanol-ether. 1-Ethyl-3-carboethoxy-4-oxo-7-cyclohexyl-1,4 -dihydroquinoline, thus obtained, melts at 176°-178°C.

Workup

  1. customrises to 35°C
  2. customa homogeneous solution is produced
  3. stirringthe mixture is stirred for a further 21/2hours at 55°C
  4. stirringwhilst stirring
  5. filtrationThe resulting precipitate is filtered off
  6. washwell washed with water
  7. customrecrystallised from ethanol-ether

Sources & evidence

ORD record
ord-b5fb2b1df1de48e0aa365e485ee2339e
Source dataset
uspto-grants-1976_06
Patent number
US03960868

Reaction notes

Loading…