Water → HCID 21533397, compound

HRID 1657451Notes

Reaction equation

HRID 1657451 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][C:12]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[CH:11][CH:10]=2)([O:3][CH2:4]C)=[O:2].[Na].O.[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO>[CH2:25]([N:8]1[C:9]2[C:14](=[CH:13][C:12]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:11][CH:10]=2)[C:15](=[O:16])[C:6]([C:1]([O:3][CH3:4])=[O:2])=[CH:7]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 5360545SodiumHCID 178469506HCID 178469506, compound

Product 1

HCID 21533397HCID 21533397, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14 g of 3-carboethoxy-4-hydroxy-6-cyclohexyl-quinoline are added to a solution of 1.45 g of sodium in 150 ml of absolute methanol, whilst stirring, and the mixture is heated to the boil for 1 hour, with exclusion of water. 7.15 g of benzyl chloride are then added dropwise to the reaction mixture, which is boiled for a further 5 hours under reflux. It is then evaporated to dryness in vacuo and the residue is partitioned between 4 times 500 ml of chloroform and 500 ml of 1 N potassium hydroxide solution at 0°C. The organic phases are washed with twice 500 ml of water, dried over sodium sulphate and evaporated to dryness in vacuo. Repeated crystallisation of the evaporation residue from ethanol gives 1-benzyl-3-carbomethoxy-4-oxo-6-cyclohexyl-1,4-dihydroquinoline of melting point 211°-213°C.

Workup

  1. temperatureunder reflux
  2. customIt is then evaporated to dryness in vacuo
  3. customthe residue is partitioned between 4 times 500 ml of chloroform and 500 ml of 1 N potassium hydroxide solution at 0°C
  4. washThe organic phases are washed with twice 500 ml of water
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness in vacuo
  7. customcrystallisation of the evaporation residue from ethanol

Sources & evidence

ORD record
ord-e81a2e51f9b94c039754cd3291206a9c
Source dataset
uspto-grants-1976_06
Patent number
US03960868

Reaction notes

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