Ethanol → (1H-Indol-5-yl)acetic acid

HRID 330190Notes

Reaction equation

HRID 330190 reaction equation
CC1C=CC(S([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17](CC#N)[CH:18]=3)[CH:13]=[CH:12]2)(=O)=O)=CC=1.[OH-:23].[Na+].[CH2:25]([OH:27])[CH3:26]>>[NH:11]1[C:19]2[C:14](=[CH:15][C:16]([CH2:26][C:25]([OH:23])=[O:27])=[CH:17][CH:18]=2)[CH:13]=[CH:12]1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14882502HCID 14882502, compound

Product 1

HCID 18399719(1H-Indol-5-yl)acetic acidYield 68%

Procedure

A solution of 1-(4-methylphenylsufonyl)indole-6-acetonitrile (9.5 g) in ethanol (58 ml) was treated with 20% (w/v) sodium hydroxide (58 ml) and heated to reflux for 2.5 hr. The ethanol was evaporated and the aqueous residue was slowly acidified at 0° with concentrated hydrochloric acid. The white precipitate was collected by filtration, washed with water and dried under vacuum to give indole-5-acetic acid (4.1 g, 68%) as an ivory powder: NMR (250 MHz, DMSO-d6): 3.57(s, 2H, ArCH2), 9.65(dd, 1H, H6 -indole), 7.40(s, 1H, H4 -indole).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.5 hr
  3. customThe ethanol was evaporated
  4. customwas slowly acidified at 0° with concentrated hydrochloric acid
  5. filtrationThe white precipitate was collected by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-cba7b09e878f43bc849c750b0ed87f2d
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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