Methanol → [7-(Benzyloxy)-1H-indol-3-yl]acetic acid

HRID 1351943Notes

Reaction equation

HRID 1351943 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C:19]#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:21].[Na+].C[OH:24]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C:19]([OH:24])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 23071170HCID 23071170, compound

Product 1

HCID 23071100[7-(Benzyloxy)-1H-indol-3-yl]acetic acidYield 86%

Procedure

Under nitrogen atmosphere, to a suspension of (7-(benzyloxy)-1H-indol-3-yl)acetonitrile (13.2 g, 50.3 mmol) in methanol (400 mL) is added 10N aqueous sodium hydroxide solution (130 mL), and the mixture is refluxed for 5 hours. The reaction solution is cooled to room temperature, and methanol alone is distilled off. The pH value of the resultant is adjusted to pH 1 with conc. hydrochloric acid while the mixture is cooled with ice. The precipitates are collected by filtration, and dissolved in chloroform, and dried over anhydrous sodium sulfate. The solvent is evaporated to give (7-(benzyloxy)-1H-indol-3-yl)acetic acid (12.2 g, 43.4 mmol, yield: 86%).

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. distillationmethanol alone is distilled off
  3. temperatureis cooled with ice
  4. filtrationThe precipitates are collected by filtration
  5. dissolutiondissolved in chloroform
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent is evaporated

Sources & evidence

ORD record
ord-e1101e469a5d4545b1ff519bccee5c06
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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