Nitric Acid → 5-Nitroisoindoline

HRID 1919026Notes

Reaction equation

HRID 1919026 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[N+:10]([O-])([OH:12])=[O:11]>OS(O)(=O)=O>[N+:10]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH2:3][NH:2][CH2:1]2)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 422478Isoindoline

Product 1

HCID 64244695-NitroisoindolineYield 51%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To the suspension of isoindoline (2 g, 16.8 mmol) in 98% H2SO4 (10 mL) was added dropwise the mixture of concentrated nitric acid (2 mL) and 98% sulfuric acid (2 mL) at 0° C. The mixture was stirred at 0° C. for 45 minutes. The resulting yellow solution was then poured into ice water. The white solid precipitate was collected by filtration. The solid was washed with water (20 mL×2) and dried in vacuum to afford 231a as a white solid (700 mg, 51%). MS: [M+H]+ 165.

Workup

  1. additionwas added dropwise
  2. filtrationThe white solid precipitate was collected by filtration
  3. washThe solid was washed with water (20 mL×2)
  4. customdried in vacuum

Sources & evidence

ORD record
ord-bc3740b0f8314fdbbc5cb0bb6d1df41d
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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