Water → 3-(carboxymethyl)-1H-indole-2-carboxylic acid

HRID 484110Notes

Reaction equation

HRID 484110 reaction equation
[C:1]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][C:16]([O:18]CC)=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)([O:3]CC)=[O:2].[OH-].[Na+].O>C(O)C>[C:1]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11821846HCID 11821846, compound

Product 1

HCID 6725473-(carboxymethyl)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-Carboethoxy-3-indoleacetate (0.7 gm) in absolute ethanol (10 ml) was combined with 50% aqueous sodium hydroxide. The mixture was heated to reflux on a steam bath for 15 minutes. The resulting solution was poured into water (50 ml) and the aqueous solution was washed with ether (2×30 ml). The aqueous solution was made acidic by the addition of concentrated hydrochloric acid and chilled to effect crystallization. The resulting white solid was recovered by filtration to provide the product. Analytical data are reported in Table I.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux on a steam bath for 15 minutes
  3. washthe aqueous solution was washed with ether (2×30 ml)
  4. additionThe aqueous solution was made acidic by the addition of concentrated hydrochloric acid
  5. temperaturechilled
  6. customcrystallization
  7. filtrationThe resulting white solid was recovered by filtration
  8. customto provide the product

Sources & evidence

ORD record
ord-ab1b5c48717141c4bac2d32a26554290
Source dataset
uspto-grants-1993_07
Patent number
US05229413

Reaction notes

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