Phthalimide → 2H-Isoindole-2-carbonitrile, 1,3-dihydro-1,3-dioxo-

HRID 1587038Notes

Reaction equation

HRID 1587038 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.[N:12]#[C:13]Br.C(N(CC)CC)C>CC(C)=O>[O:6]=[C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1](=[O:11])[N:5]1[C:13]#[N:12]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 8471TriethylamineHCID 10476Cyanogen Bromide

Product 1

HCID 109974912H-Isoindole-2-carbonitrile, 1,3-dihydro-1,3-dioxo-Yield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 25 mL round-bottomed flask was added phthalimide (1.47 g, 10.0 mmol), cyanogen bromide (1.27 g, 12.0 mmol), and 10 mL of reagent grade acetone. The resulting mixture was cooled using an ice/salt bath while triethylamine (1.8 mL, 12.8 mmol) was added dropwise over a 2 minute period. After 15 minutes, the mixture was transferred to a separatory funnel and partitioned between ethyl acetate and water. The organic phase was washed with water, saturated brine, dried (MgSO4), and filtered. The solution was decolorized with activated charcoal, and concentrated to give a brown solid. This material was recrystallized from ethyl acetate to give 1.32 g (77%) of a brown crystalline solid, mp 189°-191° C. (reported in Zh. Org. Khim. 1977, 13, 968 as 190° C.): IR (nujol) 2258 (nitrile), 1755 (carbonyl) cm-1 ; 1H NMR (200 MHz, DMSO) δ 8.05-8.15 (m, 4); 13C NMR (50 MHz, DMSO) δ 162.61, 136.35, 130.76, 125.03, 102.86.

Workup

  1. temperatureThe resulting mixture was cooled
  2. additionwas added dropwise over a 2 minute period
  3. customthe mixture was transferred to a separatory funnel
  4. custompartitioned between ethyl acetate and water
  5. washThe organic phase was washed with water, saturated brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown solid
  10. customThis material was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1ff90f27b47b472f87998d02b6c6fc92
Source dataset
uspto-grants-1993_06
Patent number
US05216173

Reaction notes

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