Ethanol → HCID 21938641, compound

HRID 1596643Notes

Reaction equation

HRID 1596643 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)[CH3:2].C([OH:15])C.[OH-].[K+]>O>[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]([NH2:8])=[C:5]([CH2:6][C:7]([OH:12])=[O:15])[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 101541895-Ethyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 21938641HCID 21938641, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Ethyloxindole (˜54 g, ˜335 mmol), ethanol (750 ml), water (150 ml) and potassium hydroxide (65 g, 1.62 mol) are combined and heated at reflux for 3 days. The mixture is allowed to cool and then filtered through a bed of Celite. The filtrate is concentrated under reduced pressure, water is added and the pH adjusted to 6.5. The precipitate is filtered off, washed with water and dried in an oven overnight to yield 5-ethyl-2-aminophenylacetic acid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 days
  3. temperatureto cool
  4. filtrationfiltered through a bed of Celite
  5. concentrationThe filtrate is concentrated under reduced pressure, water
  6. additionis added
  7. filtrationThe precipitate is filtered off
  8. washwashed with water
  9. customdried in an oven overnight

Sources & evidence

ORD record
ord-2b6feed671554ddc83ed8339dc5cfb7b
Source dataset
uspto-grants-2001_09
Patent number
US06291523B1

Reaction notes

Loading…