Sodium Hydroxide → HCID 13206065, compound

HRID 1583945Notes

Reaction equation

HRID 1583945 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]([CH3:21])[C:16]([O:18]CC)=[O:17])[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9]([CH3:14])([CH3:13])[CH:8]=[CH:7]2.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]([CH3:21])[C:16]([OH:18])=[O:17])[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9]([CH3:14])([CH3:13])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20257369HCID 20257369, compound2×

Product 1

HCID 13206065HCID 13206065, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.0 g of ethyl 2-(8-chloro-1,2-dihydro-1,2,2-trimethylquinolin-6-yl)propionate (Compound 18) were added to a mixture of 40 ml of ethanol and 10% aqueous solution of sodium hydroxide. The solution was heated and refluxed for 4 hours. Ethanol was distilled off and the reaction mixture was diluted with water and washed with ether. The water layer was made weakly acidic by the addition of hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from hexane to give 2.3 g of 2-(8-chloro-1,2-dihydro-1,2,2-trimethylquinolin-6-yl)propionic acid (Compound 34).

Workup

  1. temperatureThe solution was heated
  2. temperaturerefluxed for 4 hours
  3. distillationEthanol was distilled off
  4. additionthe reaction mixture was diluted with water
  5. washwashed with ether
  6. additionThe water layer was made weakly acidic by the addition of hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-06792174175d432981449af6334ab926
Source dataset
uspto-grants-1985_11
Patent number
US04555513

Reaction notes

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