Methanol → HCID 12805188, compound

HRID 1906218Notes

Reaction equation

HRID 1906218 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][C:24]([OH:26])=[O:25])[CH:21]=2)[NH:16][CH:15]=1.[CH3:27]O>S(=O)(=O)(O)O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:21]=2)[NH:16][CH:15]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 12805187HCID 12805187, compound

Product 1

HCID 12805188HCID 12805188, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-acetic acid (1 g) in methanol (50 ml) containing sulphuric acid (2 drops) was boiled under reflux for 1.5 h under nitrogen. Removal of the solvent gave a solid (1.2 g). Part of this material (0.5 g) was purified by column chromatography (Whatman MFC silica, 25 g). Elution with ethyl acetate-light petroleum (1:1) gave the title compound as yellow crystals (0.4 g) m.p. 121°-124°.

Workup

  1. temperatureunder reflux for 1.5 h under nitrogen
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-05569481297a4546a4c28cc56d97b6c3
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

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