Nitric Acid → 4-Nitrophthalimide

HRID 1806213Notes

Reaction equation

HRID 1806213 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.S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18]>>[N+:17]([C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[C:1](=[O:11])[NH:5][C:4]2=[O:6])([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 6809Phthalimide

Product 1

HCID 69694-NitrophthalimideYield 61.3%

Conditions

Temperature
0 °C

Procedure

In a dried 50 mL two necked round-bottom flask equipped with an addition funnel and CaCl2 drying tube was placed 2.0 g (13.6 mmol) of phthalimide. The flask was then cooled to 0° C. in a salt and ice bath. An ice cold mixture of concentrated sulfuric acid and fuming nitric acid (1:1 v/v) 8 mL was gradually added with constant stirring. The mixture was then stirred for 30 min. at 0° C. and allowed to slowly warm to room temperature with stirring over a period of 1 h. The reaction mixture was then poured into ice. The resulting solid product was filtered and dried to give 1.6 g (61.3%) of 5-nitro-1H-isoindole-1,3(2H)-dione as a yellow colour solid.

Workup

  1. additionwas gradually added with constant stirring
  2. temperatureto slowly warm to room temperature
  3. stirringwith stirring over a period of 1 h
  4. additionThe reaction mixture was then poured into ice
  5. filtrationThe resulting solid product was filtered
  6. customdried

Sources & evidence

ORD record
ord-76dbe683547e4416b4f2158c48794d68
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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