Water → 2-(4-Diethylamino-but-2-ynyl)-isoindole-1,3-dione

HRID 1620545Notes

Reaction equation

HRID 1620545 reaction equation
Cl[CH2:2][C:3]#[C:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18].O>C(#N)C>[CH2:17]([N:19]([CH2:20][CH3:21])[CH2:2][C:3]#[C:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 2375372-(4-chlorobut-2-yn-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 443855092-(4-Diethylamino-but-2-ynyl)-isoindole-1,3-dioneYield 48.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-chlorobut-2-yn-1-yl)-1H-isoindole-1,3(2H)-dione (200 mg) in acetonitrile (3 mL) was added diethylamine (188 mg) at room temperature. The reaction mixture was stirred at room temperature for 4 hr, and added to water at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (112 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f875eabe0269457aabbd2ab09d9b45f0
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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