Potassium Hydroxide → 5-Methoxy--methyl-3-(1-methylethoxy)-1H-indole-2-carboxylic acid

HRID 653152Notes

Reaction equation

HRID 653152 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:20])[C:7]2[C:12]([C:13]=1[O:14][CH:15]([CH3:17])[CH3:16])=[CH:11][C:10]([O:18][CH3:19])=[CH:9][CH:8]=2)=[O:4].[OH-].[K+]>>[CH3:19][O:18][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]([CH3:20])[C:5]([C:3]([OH:4])=[O:2])=[C:13]2[O:14][CH:15]([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 13885830HCID 13885830, compound

Product 1

HCID 138857995-Methoxy--methyl-3-(1-methylethoxy)-1H-indole-2-carboxylic acidYield 47%

Procedure

Prepared by the saponification procedure described in Example 7 from 41.2 g (0.15 mole) of 5-methoxy-1-methyl-3-(1-methylethoxy)-1H-indole-2-carboxylic acid methyl ester and 16.7 g (0.30 mole) of potassium hydroxide. The crude acid product was 18.3 g (47% yield). A sample recrystallized from aqueous 2-methoxyethanol was analytically pure, mp 110°-112° C.

Workup

  1. customPrepared by the saponification procedure
  2. customA sample recrystallized from aqueous 2-methoxyethanol

Sources & evidence

ORD record
ord-a9e59446fd884dd38fb92e098817c8f9
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

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