N-Propylphthalimide → 3-Hydroxy-2-propyl-2,3-dihydroisoindol-1-one

HRID 1792905Notes

Reaction equation

HRID 1792905 reaction equation
[CH2:1]([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])[CH2:2][CH3:3]>CO.[BH4-].[K+]>[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[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 79215N-Propylphthalimide

Product 1

HCID 40135343-Hydroxy-2-propyl-2,3-dihydroisoindol-1-oneYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4192641Potassium borohydrideSolvent

Conditions

Temperature
20 °C

Procedure

3-Hydroxy-2-propyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 1.5 g of N-propylphthalimide in 25 cm3 of methanol and 0.48 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the region of 0° C. and distilled water is added dropwise. The methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 35° C. and the residue is cooled to 0° C. The precipitate obtained is filtered off and then washed with cold water. The solid is taken up in dichloromethane and the solvent is then evaporated to dryness under reduced pressure (2 kPa) at a temperature in the region of 35° C. 1.0 g of 3-hydroxy-2propyl-2,3-dihydroisoindol-1-one is thus obtained in the form of a beige-colored powder. (Rf=0.6, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (30/70 by volume)).

Workup

  1. custom3-Hydroxy-2-propyl-2,3-dihydroisoindol-1-one is prepared
  2. temperatureis then cooled to a temperature in the region of 0° C.
  3. distillationdistilled water
  4. additionis added dropwise
  5. customThe methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 35° C.
  6. temperaturethe residue is cooled to 0° C
  7. customThe precipitate obtained
  8. filtrationis filtered off
  9. washwashed with cold water
  10. customthe solvent is then evaporated to dryness under reduced pressure (2 kPa) at a temperature in the region of 35° C

Sources & evidence

ORD record
ord-b899b9d8d8054722b2f738da334d7782
Source dataset
uspto-grants-2006_07
Patent number
US07078428B2

Reaction notes

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