Phthalimide → 4-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]benzonitrile

HRID 1663230Notes

Reaction equation

HRID 1663230 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>CN(C)C=O>[O:17]=[C:15]1[C:14]2[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](=[O:22])[N:16]1[CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 28008154-(2-Hydroxyethyl)benzonitrile

Product 1

HCID 674369234-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]benzonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, a solution of 4-(2-hydroxy-ethyl)-benzonitrile [Helv. Chim. Acta 64 (1981) 1688-1703] (4.49 g, 30.5 mmol), phthalimide (4.94 g, 33.55 mmol), triphenylphosphine (8.8 g, 33.55 mmol) and dimethyl formamide (100 mL) was stirred at 0° C. for 20 minutes, then diethyl azodicarboxylate (7.59 mL, 48.8 mmol) was added dropwise at 0° C. The so obtained reaction mixture was stirred at room temperature overnight, then poured into ice-water (740 mL). The precipitated product was filtered off, washed with water and dried. The crude product was recrystallized from 2-propanol to yield 7.83 g (93%) of the title compound as a yellow solid.

Workup

  1. customThe so obtained
  2. customreaction mixture
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water
  5. customdried
  6. customThe crude product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-fee2f4aa21cd4c0e84407a4ac8d38c7a
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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