Trifluoroacetic acid → Phthalimidine

HRID 1818767Notes

Reaction equation

HRID 1818767 reaction equation
[C:1]1(=O)[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C(O)(C(F)(F)F)=O>C(OCC)(=O)C.[Pd]>[C:4]1(=[O:6])[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:1][NH:5]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 6809Phthalimide

Product 1

HCID 10199PhthalimidineYield 7.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of phthalimide (1.0 g, 6.8 mmol) and TFA (5 mL) in ethyl acetate (100 mL) was added 10% Pd—C (1 g). The reaction mixture was hydrogenated at 55 psi for 2 days. Catalyst was then filtered through diatomaceous earth (Celite®) and the filtrate was concentrated to give yellowish solid as crude product (0.37 g). 120 mg of them was then purified by Prep. TLC (eluted with dichloromethane) to give pure 2,3-dihydro-isoindol-1-one (65 mg).

Workup

  1. filtrationCatalyst was then filtered through diatomaceous earth (Celite®)
  2. concentrationthe filtrate was concentrated
  3. customto give yellowish solid as crude product (0.37 g)
  4. custom120 mg of them was then purified by Prep
  5. washTLC (eluted with dichloromethane)

Sources & evidence

ORD record
ord-4d62a03c13804ab0826c2ca204400d14
Source dataset
uspto-grants-2009_10
Patent number
US07601686B2

Reaction notes

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