Sodium Hydroxide → 2-(6-Quinolinyloxy)-2-(ethoxy)acetic acid

HRID 2222288Notes

Reaction equation

HRID 2222288 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([O:18][CH2:19][CH3:20])[C:13]([O:15]CC)=[O:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O.CO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([O:18][CH2:19][CH3:20])[C:13]([OH:15])=[O:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21923123Ethyl 2-(6-quinolinyloxy)-2-(ethoxy)acetate

Product 1

HCID 219231312-(6-Quinolinyloxy)-2-(ethoxy)acetic acidYield 44.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-(6-quinolinyloxy)-2-(ethoxy)acetate (3.68 g) was added to a solution of sodium hydroxide (0.589 g) in water (10 ml) and methanol (30 ml) and stirred for 5 minutes. The solution was evaporated under reduced pressure, water added and the aqueous phase was washed with ethyl acetate. The aqueous phase was acidified with hydrochloric acid and extracted with ethyl acetate. The extracts were combined, dried over magnesium sulphate and evaporated under reduced pressure to give 2-(6-quinolinyloxy)-2-(ethoxy)acetic acid (1.47 g) as a cream solid.

Workup

  1. customThe solution was evaporated under reduced pressure, water
  2. additionadded
  3. washthe aqueous phase was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-82529aeb338a4274bc76c065460df362
Source dataset
uspto-grants-2008_05
Patent number
US07371764B2

Reaction notes

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