2-{(E)-2-[3-amino-5-(trifluoromethyl)phenyl]vinyl}-1H-isoindole-1,3(2H)-dione → Phthalimide

HRID 1640128Notes

Reaction equation

HRID 1640128 reaction equation
NC1C=C(/C=C/[N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])C=C(C(F)(F)F)C=1.[H][H]>[Pd].C1COCC1>[C:15]1(=[O:24])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22](=[O:23])[NH:14]1

Participants

5

Reactant 2

HCID 591349702-{(E)-2-[3-amino-5-(trifluoromethyl)phenyl]vinyl}-1H-isoindole-1,3(2H)-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 6809PhthalimideYield 41.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 2-{(E)-2-[3-amino-5-(trifluoromethyl)phenyl]vinyl}-1H-isoindole-1,3(2H)-dione (1.99 g, 5.98 nunol) and Pd/C (0.20 g, 10% by weight) in ETOH (123 mL) and THF (88 mL) was allowed to stir under 50 psi of hydrogen at rt until reaction was judged to be complete. The mixture was filtered through Celite and concentrated. The residue was purified by column chromatography to give 2-12-[3-amino-5-(trifluoromethyl)phenyl]ethyl)-1H-isoindole-1,3(2H)-dione (365 mg, 16% yield). LCMS: (FA) ES+ 335.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-62e8a4d58e894cdfb2cb254d20db9221
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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