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

HRID 564977Notes

Reaction equation

HRID 564977 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-c9a35eb550b0418a8322db2637d2740d
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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