1H-Indole-2-acetic acid, 1-methyl-, ethyl ester → 2-(1-Methyl-1H-indol-2-yl)acetic acid

HRID 2050480Notes

Reaction equation

HRID 2050480 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][C:12]([O:14]CC)=[O:13]>[OH-].[Na+]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][C:12]([OH:14])=[O:13]

Participants

3

Reactant 1

HCID 122340421H-Indole-2-acetic acid, 1-methyl-, ethyl ester

Product 1

HCID 8259602-(1-Methyl-1H-indol-2-yl)acetic acidYield 48.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of ethyl 1-methyl-1H-indole-2-acetate (5.0 g) and 2N sodium hydroxide (50 ml) was heated to reflux for 4 h. After cooling, the reaction mixture was extracted with ethyl acetate (2x50 ml) and theresulting aqueous solution was made acidic (pH 1) by addition of 2N hydrochloric acid. The resulting solid was filtered off, washed with ether (100 ml) and dried in vacuo to give the title compound (2.1 g), m.p. 146-148°.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with ethyl acetate (2x50 ml)
  5. additionby addition of 2N hydrochloric acid
  6. filtrationThe resulting solid was filtered off
  7. washwashed with ether (100 ml)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-eeeec50ae5124b9281e930f6c80006af
Source dataset
uspto-grants-1991_05
Patent number
US05013733

Reaction notes

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