Phthalic Anhydride → 2-[3-fluoro-5-(pyridin-3-yloxy)phenyl]-1H-isoindol-1,3(2H)-dione

HRID 1809831Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([O:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:8]=1)[NH2:5].[C:16]1(=O)[O:21][C:19](=[O:20])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:19](=[O:20])[C:18]3[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16]2=[O:21])[CH:6]=[C:7]([O:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-fluoro-5-(pyridine-3-yloxy)aniline (330 mg) in acetic acid (5.0 ml), 160 mg of phthalic anhydride was added, the reaction solution was stirred overnight at 100° C. The reaction solution was cooled, followed by adding a saturated aqueous sodium bicarbonate solution and extracting the mixture with chloroform. The combined organic layers were washed with water and a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel chromatography to yield the title compound as a white solid.

Workup

temperatureThe reaction solution was cooled
extractionextracting the mixture with chloroform
washThe combined organic layers were washed with water
dry with materiala saturated saline solution and dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resultant residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-a15add5faf454be4b73386cc69737281
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362052B2

Reaction notes

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