Water → 3-hydroxy-2-methyl-2,3-dihydro-1H-isoindol-1-one
Reaction equation
[BH4-].[K+].[CH3:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].O>CO>[OH:9][CH:8]1[C:7]2[C:6](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:14])[N:4]1[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
3.4 g of potassium borohydride are added slowly to a suspension of 10 g of N-methylphthalimide in 220 cm3 of methanol under an inert atmosphere. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours, followed by dropwise addition of 200 cm3 of distilled water. The solvent is then partially evaporated off (about 120 cm3) under reduced pressure (2 kPa) at a temperature in the region of 35° C., and the residue is diluted with 400 cm3 of distilled water. The mixture is extracted with 400 cm3 of ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C. 4.5 g of 3-hydroxy-2-methyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a white powder melting at 130° C.
Workup
- customThe solvent is then partially evaporated off (about 120 cm3) under reduced pressure (2 kPa) at a temperature in the region of 35° C.
- additionthe residue is diluted with 400 cm3 of distilled water
- extractionThe mixture is extracted with 400 cm3 of ethyl acetate
- dry with materialThe organic phase is dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C
Sources & evidence
- ORD record
- ord-c8ce6b1b5da54013bf86ee74e0ca34d7
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589117B2
Reaction notes
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