Ethanol → HCID 21938641, compound

HRID 382487Notes

Reaction equation

HRID 382487 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-a28d412d8ad440fa9f509ea5eb63a2b3
Source dataset
uspto-grants-2001_10
Patent number
US06310099B1

Reaction notes

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