Water → 2-(2-oxobutyl)isoindoline-1,3-dione

HRID 1730390Notes

Reaction equation

HRID 1730390 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15](=[O:18])[CH2:16][CH3:17].C(Cl)(Cl)Cl.O>CN(C)C=O>[C:1]1(=[O:11])[N:5]([CH2:14][C:15](=[O:18])[CH2:16][CH3:17])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 131561-Bromo-2-butanoneHCID 24194345Phthalimide potassium salt

Product 1

HCID 114472662-(2-oxobutyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of potassium phthalimide (5.0 g, 0.027 mmole) in 25ml of dimethylformamide is added, dropwise, 3.80 g (0.025 mmole) of 1-bromobutanone. The mixture is heated for 10 hours at 80° C under nitrogen and then 150 ml of chloroform is added. The resulting mixture is poured into 30 ml of water and the organic layer is separated and washed with 10 ml of 0.2N sodium hydroxide. The resulting chloroform and dimethylformamide solution is dried over anhydrous sodium sulfate, and evaporated in vacuo to give 1-phthalimidobutanone.

Workup

  1. additionis added
  2. customthe organic layer is separated
  3. washwashed with 10 ml of 0.2N sodium hydroxide
  4. dry with materialThe resulting chloroform and dimethylformamide solution is dried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9a50b3749db446b2a1593a5b2dff8ab8
Source dataset
uspto-grants-1976_11
Patent number
US03992408

Reaction notes

Loading…