Ethanol → 5-Methyl-2,3-dihydro-1H-isoindol-1-one

HRID 1454280Notes

Reaction equation

HRID 1454280 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6](CC=CC1C=CC=CC=1)[CH2:5]2.C(O)C>CCCCCC.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2

Participants

4

Reactant 2

HCID 702EthanolHCID 68567766HCID 68567766, compound

Product 1

HCID 220646715-Methyl-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

5-Methyl-2-(phenyl-allyl)-2,3-dihydro-isoindol-1-one (3.64 g, 14.61 mmol) was taken up in a 50/50 mixture of ethanol-3M HCl (100 mL) and heated to 80EC for 12 h. The reaction mixture was cooled and the ethanol was removed under reduced pressure. The aqueous layer was extracted three times with ethyl acetate and the combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (1:1 hexane/ethyl acetate) Yield 1.40 g. 1H NMR (CDCl3, 300 MHz): δ 2.51 (s, 3H), 4.48 9s, 2H), 7.27-7.36 (m, 2H), 7.75 (d, J=8 Hz, 1H).

Workup

  1. temperatureheated to 80EC for 12 h
  2. temperatureThe reaction mixture was cooled
  3. customthe ethanol was removed under reduced pressure
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe solution was filtered
  8. customthe solvent removed under reduced pressure
  9. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-e000b96a640b43888464a0a8d008eee0
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

Loading…