4-Nitrophthalimide → HCID 15707391, compound

HRID 1587039Notes

Reaction equation

HRID 1587039 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[N:15]#[C:16]Br.C(N(CC)CC)C>CC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:13][CH:14]=1)[C:8](=[O:9])[N:10]([C:16]#[N:15])[C:11]2=[O:12])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69694-NitrophthalimideHCID 8471TriethylamineHCID 10476Cyanogen Bromide

Product 1

HCID 15707391HCID 15707391, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 25 mL round-bottomed flask was charged with 4-nitrophthalimide (0.96 g, 5.0 mmol), cyanogen bromide (0.64 g, 6.0 mmol), and 10 mL of reagent grade acetone. The resulting suspension was cooled using an ice/salt bath, and triethylamine (1.0 mL, 7.1 mmol) was added dropwise over a 4 minute period. The mixture was allowed to stir for 20 minutes before being partitioned between ethyl acetate and water. The organic phase was washed with water, saturated brine, dried (MgSO4), and concentrated to give 0.95 g of a yellow solid. This material was recrystallized from ethyl acetate to afford 0.65 g (60%) of yellow crystals, mp 209.5°-210.5° C. (reported in Zh. Org. Khim. 1977, 13, 968 as 215° C.): IR (nujol) 2261 (nitrile), 1811 (carbonyl), 1769 (carbonyl), 1533 (nitro), 1343 (nitro) cm-1 ; 1H NMR (200 MHz, DMSO) δ 8.34 (d, 1, J=8.9 Hz), 8.70-8.78 (m, 2); 13C NMR (50 MHz, DMSO) δ 161.15, 160.92, 152.34, 135.19, 132.10, 131.16, 126.48, 119.76, 102.26; GC/MS (relative intensity) 217 (77.8), 149 (71.7), 103 (64.4), 75 (100), 74 (52.7).

Workup

  1. temperatureThe resulting suspension was cooled
  2. custombefore being partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water, saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b93c6a65b9214456993f393cc894332b
Source dataset
uspto-grants-1993_06
Patent number
US05216173

Reaction notes

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