Potassium Hydroxide → (5-fluoro-2-methyl-1H-indol-3-yl)acetic acid

HRID 346807Notes

Reaction equation

HRID 346807 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][C:7]=1[CH3:16])C.[OH-].[K+]>CO.O>[F:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:16])=[C:6]2[CH2:5][C:4]([OH:17])=[O:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 11665843Ethyl (5-fluoro-2-methyl-1H-indol-3-yl)acetate

Product 1

HCID 2772338(5-fluoro-2-methyl-1H-indol-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

This ester (4.5 g, 0.019 mol.) was added to a solution of KOH (2.13 g, 38 mmol.) in methanol (100 ml), and the mixture was heated at reflux for 30 min. For working up, the mixture was diluted with water (100 ml) and methanol was distilled off using a rotary evaporator. The aqueous phase was adjusted to pH 4 with 2M HCl and stored for 2 h at 4° C. The white solid that precipitated was filtered off with suction and washed with methanol. (5-Fluoro-2-methyl-1H-indol-3-yl)acetic acid was obtained in a yield of 3.25 g (m.p. 136–138° C.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 min
  3. distillationwas distilled off
  4. customa rotary evaporator
  5. customThe white solid that precipitated
  6. filtrationwas filtered off with suction
  7. washwashed with methanol

Sources & evidence

ORD record
ord-ec0baa94779c4a43a1377b4ed448385f
Source dataset
uspto-grants-2007_02
Patent number
US07173045B2

Reaction notes

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