Nitric Acid → 5-Nitroisoindoline

HRID 604626Notes

Reaction equation

HRID 604626 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].[OH-].[Na+]>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

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 422478Isoindoline

Product 1

HCID 64244695-Nitroisoindoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of isoindoline (2 g, 16.8 mmol) at 0° C., was added slowly concentrated H2SO4 (10 mL). Then a mixture of 70% HNO3 (2.1 mL, 33.6 mmol) and concentrated H2SO4 (2 mL) was added. After addition the mixture was stirred at 0° C. for 30 min. The reaction mixture was poured into ice water. The mixture was carefully neutralized with 50% aq. NaOH to pH 10 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 5-nitroisoindoline as a brown solid. LCMS calc.=165.1; found=164.9 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.11 (d, J=8.0 Hz, 2H); 7.39 (d, J=7.8 Hz, 1H); 4.33 (s, 4H); 2.31 (br s, 1H).

Workup

  1. additionwas added
  2. additionAfter addition the mixture
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f294928a2584f848e7e3c080f138527
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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