Sodium Hydroxide → (5-Methoxy-1H-indol-1-yl)acetic acid

HRID 571191Notes

Reaction equation

HRID 571191 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15]C)=[O:14])[CH:7]=[CH:6]2.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 43152078HCID 43152078, compound

Product 1

HCID 17571571(5-Methoxy-1H-indol-1-yl)acetic acidYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(5-methoxy-1H-indol-1-yl)acetate (745 mg, 3.40 mmol) in MeOH (20 ml), aqueous 4N sodium hydroxide (935 μl, 3.74 mmol) was slowly added and the reaction was stirred at room temperature for 1 hour. The solvent was removed and the residue was partitioned between ethyl acetate and water. The aqueous phase was acidified with 2.5M HCl and extracted with ethyl acetate. This organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (510 mg, 2.485 mmol, 73% yield). MS/ESI+ 206.1 [MH]+.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionextracted with ethyl acetate
  4. washThis organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a64d57c7fb974333b8f93c6ce68f49a9
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

Loading…