Sodium Hydroxide → 1-methylindole-2,7-dicarboxylic Acid

HRID 1067765Notes

Reaction equation

HRID 1067765 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[N:12]([CH3:14])[C:11]([C:15]([O:17]CC)=[O:16])=[CH:10]2)([O:3]C)=[O:2].[OH-].[Na+]>C(O)C>[CH3:14][N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[C:1]([OH:3])=[O:2])[CH:10]=[C:11]1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10825291Ethyl 7-carbomethoxy-1-methyl-2-indolecarboxylate

Product 1

HCID 108465121-methylindole-2,7-dicarboxylic AcidYield 107.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.20 g (19.9 mmol) of ethyl 7-carbomethoxy-1-methyl-2-indolecarboxylate, 90 ml of 2N sodium hydroxide and 150 ml of ethanol was refluxed for 3 hours. The reaction mixture was concentrated under reduced pressure and ice water was added to the residue. 2N hydrochloric acid was added to acidify the reaction mixture. The precipitated solid was filtered and dried under reduced pressure to give 4.70 g (>99%) of 1-methylindole-2,7-dicarboxylic acid.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure and ice water
  3. additionwas added to the residue
  4. addition2N hydrochloric acid was added
  5. filtrationThe precipitated solid was filtered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-abc21a79c3b040589527faeaf14517b9
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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