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

HRID 1071520Notes

Reaction equation

HRID 1071520 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

Conditions

Temperature
80 °C

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

Sources & evidence

ORD record
ord-9288f22e054545298bfb9abd0505a57e
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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