N-prop-2-ynylphthalimide → 3-Hydroxy-2-(prop-2-yn-1-yl)-2,3-dihydro-1H-isoindol-1-one

HRID 1032766Notes

Reaction equation

HRID 1032766 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])[C:2]#[CH:3].[BH4-].[Na+]>C(O)C>[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][C:2]#[CH:3]

Participants

4

Reactant 2

HCID 81644N-prop-2-ynylphthalimideHCID 4311764Sodium borohydride

Product 1

HCID 148519453-Hydroxy-2-(prop-2-yn-1-yl)-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 g of N-propargylphthalimide and 2 g of sodium borohydride in 100 ml of ethanol was heated on the steam bath for 15 minutes with stirring. The resulting solution was concentrated under reduced pressure to one third of the volume and the product was crystallized by addition of ice and saturated sodium bicarbonate solution. The precipitated crystals of the title compound were collected by filtration, washed with water and sucked dry. After drying in vacuum they had m.p. 157°-159° C.

Workup

  1. temperaturewas heated on the steam bath for 15 minutes
  2. concentrationThe resulting solution was concentrated under reduced pressure to one third of the volume
  3. customthe product was crystallized by addition of ice and saturated sodium bicarbonate solution
  4. filtrationThe precipitated crystals of the title compound were collected by filtration
  5. washwashed with water
  6. customsucked dry
  7. customAfter drying in vacuum they

Sources & evidence

ORD record
ord-727773a2b90a44d897a9b9078f0e5ee1
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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