Water → N-(Cyanomethyl)-phthalimide

HRID 602783Notes

Reaction equation

HRID 602783 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[NH:2]1.[H-].[Na+].Cl[CH2:15][C:16]#[N:17].O>CN(C=O)C>[O:11]=[C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[N:2]1[CH2:15][C:16]#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6809PhthalimideHCID 7856ChloroacetonitrileHCID 24758Sodium hydride

Product 1

HCID 345881N-(Cyanomethyl)-phthalimideYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32 g (0.217 mol) of isoindole-1,3-dione in 160 mL of DMF were treated with 11.75 g (0.294 mol, 1.35 eq) of NaH (60% in oil) over 45 min at 0° C. 22.17 g (0.294 mol, 1.35 eq) of chloro-acetonitrile were added, and the reaction was stirred over night. The reaction mixture was poured into 1.5 L of water, and the precipitate was collected by filtration, washed with Et2O and dried under high vacuum to afford 36.1 g (89%) of (1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetonitrile as a white solid, MS: 187 (MH+).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with Et2O
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-b303b2729d4d4207872bc5283a7f7e52
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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