Sodium Hydroxide → 1-Methyl-1H-indole-6-carboxylic acid

HRID 252833

Reaction equation

HRID 252833 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13]C)=[O:12])[CH:9]=2)[CH:4]=[CH:3]1.[OH-].[Na+]>CO.C1COCC1.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 639843Methyl N-methylindole-6-carboxylate

Product 1

HCID 198192611-Methyl-1H-indole-6-carboxylic acidYield 248.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Methyl 1-methyl-1H-indole-6-carboxylate 166 (1.24 mmol) was stirred with sodium hydroxide (0.59 g, 14.88 mmol) in a 2:2:1 mixture of methanol/THF/water (7.5 mL) for 36 hrs at rt to form a precipitate which was collected by filtration and lyophilized overnight to give the title compound 167 (0.54 g, 99% yield). MS: 175.06 (calc), 176.1 (obs).

Workup

  1. customto form a precipitate which
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5902ff32a3db45d1bd8d0c87b9ee4246
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Linked notes

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