Phthalic Anhydride → 3-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)benzeneacetic acid

HRID 1519507Notes

Reaction equation

HRID 1519507 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:17][CH:18]=1>C(O)(=O)C.CCOC(C)=O>[O:11]=[C:1]1[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:6])[N:12]1[C:13]1[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 6811Phthalic AnhydrideHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 212622833-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)benzeneacetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of phthalic anhydride (1.2 g, 8.3 mmol) and (3-aminophenyl)acetic acid (1.0 g, 6.9 mmol) in acetic acid (25 mL) was heated to reflux for 16 hours. The reaction was cooled, and diluted with 25 mL of EtOAc. A lot of solids crashed out from the solution. The solids were collected by filtration, and identified as the desired [3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]acetic acid. LC-MS (IE, m/z): 282 [M+1]+.

Workup

  1. temperatureto reflux for 16 hours
  2. temperatureThe reaction was cooled
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-e446ed2c2aa443ddbc1c3667b33f982e
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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