2-Benzyl-5-methoxy-2,3-dihydro-1H-isoindole → 2-Benzylisoindolin-5-ol

HRID 131031Notes

Reaction equation

HRID 131031 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:17]C)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:17])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 151678992-Benzyl-5-methoxy-2,3-dihydro-1H-isoindole

Product 1

HCID 597299282-Benzylisoindolin-5-olYield 49%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Combine 2-Benzyl-5-methoxy-2,3-dihydro-1H-isoindol (580.0 mg, 2.42 mmol) and 48% HBr (aq) (20 mL). Reflux the reaction for 5 hours and then cool to room temperature. Concentrate the reaction mixture under reduced pressure then add to 5 g a SCX column. Wash the column with MeOH and elute with 1N NH3-MeOH to afford 265.4 mg, 1.17 mmol (49% yield) of the title compound as a brown solid: 1H NMR (500 MHz, d-Methanol); 3.8-3.9 (4H, m), 3.91 (2H, s), 6.6-6.7 (2H, m), 7.0 (1H, d), 7.2-7.5 (4H, m); MS m/z 226 (M+1).

Workup

  1. temperatureReflux
  2. customthe reaction for 5 hours
  3. concentrationConcentrate the reaction mixture under reduced pressure
  4. additionthen add to 5 g a SCX column
  5. washWash the column with MeOH
  6. washelute with 1N NH3-MeOH

Sources & evidence

ORD record
ord-7d9d9ce54ffe48e39fb599eeb31da7cc
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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