Sodium Hydroxide → 2-[1-(4-fluorobenzyl)-1H-indol-3-yl]acetic acid

HRID 1738923Notes

Reaction equation

HRID 1738923 reaction equation
FC1C=CC(C[O:7][C:8](=[O:27])[CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:11]=2)=CC=1.[OH-].[Na+]>C(O)C>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([CH2:9][C:8]([OH:27])=[O:7])=[CH:11]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21840193[1-(4-Fluorobenzyl)indole-3-yl]acetic acid (4-fluorobenzyl)ester

Product 1

HCID 27744362-[1-(4-fluorobenzyl)-1H-indol-3-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.7 g (22.2 mMol) [1-(4-fluorobenzyl)indole-3-yl]acetic acid (4-fluorobenzyl)ester are dissolved in 50 ml ethanol. 110 ml 1N sodium hydroxide solution are added and the mixture heated for 1 hour at reflux. After cooling, the aqueous phase is washed with ether, acidulated with concentrated hydrochloric acid and the precipitate filtered.

Workup

  1. temperaturethe mixture heated for 1 hour
  2. temperatureat reflux
  3. temperatureAfter cooling
  4. washthe aqueous phase is washed with ether
  5. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-af84598adf4b4775b1f704be7c31ec12
Source dataset
uspto-grants-1999_10
Patent number
US05965582

Reaction notes

Loading…