Phthalic Anhydride → beta,beta-Dimethyl-1,3dioxo-2-isoindolinepropionic acid

HRID 852214Notes

Reaction equation

HRID 852214 reaction equation
[NH2:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[C:9]1(=O)[O:14][C:12](=[O:13])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12>C(O)C>[CH3:7][C:2]([CH3:8])([N:1]1[C:12](=[O:13])[C:11]2[C:10](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]1=[O:14])[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 27609333-Amino-3-methylbutanoic acid

Product 1

HCID 22038564beta,beta-Dimethyl-1,3dioxo-2-isoindolinepropionic acidYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

An intimate mixture of of 3-amino-3-methyl butanoic acid (27.4 g, 0.234 mol) and phthalic anhydride (38.1 g, 0.257 mol) is heated at 180° C. for 1.5 hours. After cooling, the reaction mixture is dissolved in 40 ml of ethanol and kept in a refrigerator for 54 hours. The colorless crystalline precipitate thus obtained is collected by suction and dried at 50° C. for 3 hours in a vacuum oven to give 19.2 g of β,β-dimethyl-1,3-dioxo-2-isoindolinepropionic acid (58%).

Workup

  1. temperatureAfter cooling
  2. customThe colorless crystalline precipitate thus obtained
  3. customis collected by suction
  4. customdried at 50° C. for 3 hours in a vacuum oven

Sources & evidence

ORD record
ord-50d5fd5a5980472480bcb28cdaf549b3
Source dataset
uspto-grants-2007_08
Patent number
US07253181B2

Reaction notes

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