Ethylene Glycol → 3-acetyl-1H-indole-5-carboxylic acid

HRID 1821953Notes

Reaction equation

HRID 1821953 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[C:14](=[O:16])[CH3:15])=[O:4].C(O)CO.[OH-].[K+]>O1CCCC1>[C:14]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)[NH:10][CH:9]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 11629897HCID 11629897, compound

Product 1

HCID 115574973-acetyl-1H-indole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.686 g (3.16 mmol) methyl-3-acetylindole-5-carboxylate are dissolved under heat in 10 ml tetrahydrofurane and 10 ml ethylene glycol and mixed with 7.08 g (0.13 mol) potassium hydroxide. Having stirred under reflux for 30 minutes, the reaction mixture is cooled to room temperature. The tetrahydrofurane is removed on the rotary evaporator and the solution is acidified under ice cooling with 20 ml 6N hydrochloric acid. The precipitated light violet precipitate is sucked off and dried.

Workup

  1. temperatureunder reflux for 30 minutes
  2. customThe tetrahydrofurane is removed on the rotary evaporator
  3. customdried

Sources & evidence

ORD record
ord-ef564195514c4edba2003ec56fe940af
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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