N-Methylphthalimide → 3-hydroxy-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 1453692Notes

Reaction equation

HRID 1453692 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14]>CO>[OH:13][CH:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]1[CH3:3]

Participants

4

Reactant 2

HCID 11074N-MethylphthalimideHCID 4311764Sodium borohydride2×

Product 1

HCID 27525883-hydroxy-2-methyl-2,3-dihydro-1H-isoindol-1-oneYield 32.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

NaBH4 (566 mg, 14.91 mmol) was added to a stirring solution of 2-methyl-isoindole-1,3-dione (2.0 g, 12.42 mmol) in methanol (20 mL) at 0° C. Stirring at 0° C. was maintained for 1 hour, then the reaction was warmed to room temperature. Additional NaBH4 (566 mg, 14.91 mmol) was added in order to push the reaction to completion. The reaction was then quenched with acetic acid (5 mL) and partitioned between water and dichloromethane. The organic layer was washed several times with water and concentrated under vacuum to give 659-mg of the sub-title compound as a white solid. MS: ESI (positive): 164 (M+H).

Workup

  1. temperaturewas maintained for 1 hour
  2. temperaturethe reaction was warmed to room temperature
  3. customthe reaction to completion
  4. customThe reaction was then quenched with acetic acid (5 mL)
  5. custompartitioned between water and dichloromethane
  6. washThe organic layer was washed several times with water
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-364f79b9faf2428db91b7de3833b5121
Source dataset
uspto-grants-2009_01
Patent number
US07476667B2

Reaction notes

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