Reaction #607486

ord-f7747a0545614a7db3269e1fdf0c0420

Reaction equation

O=C1OC(=O)c2ccccc21
isobenzofuran-1,3-dione
NCCC(=O)O
3-aminopropanoic acid
O=C(O)CCN1C(=O)c2ccccc2C1=O
3-(1,3-dioxoisoindolin-2-yl)propanoic acid
Yield 69.0%

Solvents

Conditions

Temperature
170°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherUpon reaction completion
  2. 2
    Extractionextracted with DCM (100 mL×3)
  3. 3
    DryingThe combined organic layers were dried over anhydrous sodium sulfate
  4. 4
    Filtrationfiltered
  5. 5
    Concentrationconcentrated under reduced pressure

Procedure

A mixture of isobenzofuran-1,3-dione (20 g, 135 mmol) and 3-aminopropanoic acid (12 g, 135 mmol) was stirred at 170° C. for 6 h. See FIG. 2. Upon reaction completion, the mixture was diluted with water and extracted with DCM (100 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 3-(1,3-dioxoisoindolin-2-yl)propanoic acid 137g (20 g, 69%) as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09326985B2uspto-grants-2016_05