Phthalic Anhydride → 2-[2-(Pyridin-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione

HRID 645912Notes

Reaction equation

HRID 645912 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.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][NH2:20]>>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][N:20]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

3

Reactant 2

HCID 6811Phthalic AnhydrideHCID 759192-Pyridineethanamine

Product 1

HCID 2313802-[2-(Pyridin-2-yl)ethyl]-1H-isoindole-1,3(2H)-dioneYield 66%

Conditions

Temperature
100 °C

Procedure

A mixture of phthalic anhydride 4 (5.0 g, 33.7 mmol) and pyridylethylamine (4.04 mL, 33.7 mmol) were heated together at 100° C. for 4 h. The resulting red oil upon cooling to room temperature yielded an off-white solid that was filtered and dried under vacuum to provide 5 as a white solid (5.6 g, 66%).

Workup

  1. temperatureThe resulting red oil upon cooling to room temperature
  2. customyielded an off-white solid
  3. filtrationthat was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-73fc9de3020547418bb5e6f27d24aa49
Source dataset
uspto-grants-2010_04
Patent number
US07705021B2

Reaction notes

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