Water → HCID 13190987, compound

HRID 1195867Notes

Reaction equation

HRID 1195867 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=1.[OH-].[Na+].O>CO>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[C:11]1[CH:21]=[CH:20][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 1201585HCID 1201585, compound

Product 1

HCID 13190987HCID 13190987, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)benzoic acid, ethyl ester (2.55 g, 0.009 mol), NaOH (20 ml), water (70 ml), and methanol (70 ml) is heated to reflux for 20 minutes when a clear solution is formed. The reaction mixture is filtered and the filtrate is carefully acidified with 4N HCl (6 ml) to pH 1.0 when a solid pptd. out. The crude 4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)benzoic acid is filtered, washed with hot CH3OH and dried to give analytical sample. Yield 1.67 g (73%); mp >295° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 20 minutes when a clear solution
  3. customis formed
  4. filtrationThe reaction mixture is filtered
  5. filtrationThe crude 4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)benzoic acid is filtered
  6. washwashed with hot CH3OH
  7. customdried
  8. customto give analytical sample

Sources & evidence

ORD record
ord-38b3a74f6d0549ef98dc5e771e205021
Source dataset
uspto-grants-1992_05
Patent number
US05112846

Reaction notes

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