Water → 7-Ethyl-1H-indole-3-carboxylic acid

HRID 2264618Notes

Reaction equation

HRID 2264618 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)[CH3:2].[OH2:12].CN([CH:16]=[O:17])C>FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[C:8]2[C:16]([OH:17])=[O:12])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 27247117-Ethylindole

Product 1

HCID 283955997-Ethyl-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 9845Trifluoroacetic anhydrideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3.0 g of 7-ethylindole in 25 mL of DMF, 3.5 mL of trifluoroacetic anhydride was added under ice cooling and the resulting mixture was stirred at room temperature for 3 hours. To the solution, 100 mL of water was added, and the precipitated solid was collected by filtration. The solid thus obtained was suspended in 100 mL of 5 M aqueous sodium hydroxide solution and the resulting suspension was stirred at 100° C. for 5 hours. After the solution was allowed to cool, it was washed twice with 30 mL of 1,2-dichloroethane. Concentrated hydrochloric acid was added to the aqueous layer to adjust the pH to pH2 and the precipitated solid was collected by filtration and washed with ether to obtain 3.14 g of 7-ethylindole-3-carboxylic acid as a beige solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customThe solid thus obtained
  3. stirringthe resulting suspension was stirred at 100° C. for 5 hours
  4. temperatureto cool
  5. washit was washed twice with 30 mL of 1,2-dichloroethane
  6. additionConcentrated hydrochloric acid was added to the aqueous layer
  7. filtrationthe precipitated solid was collected by filtration
  8. washwashed with ether

Sources & evidence

ORD record
ord-be2451e27335490784961dea90f0342a
Source dataset
uspto-grants-2010_12
Patent number
US07855225B2

Reaction notes

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