Nitric Acid → HCID 22393544, compound

HRID 1071521Notes

Reaction equation

HRID 1071521 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:12]([O-:14])=[O:13])[C:7](=[O:11])[NH:6][CH2:5]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 220646715-Methyl-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 22393544HCID 22393544, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

5-Methyl-2,3-dihydro-isoindol-1-one (1.00 g, 6.79 mmol) was taken up in sulfuric acid and cooled to 0° C. One equivalent of nitric acid was added to the solution and the mixture was allowed to slowly warm to room temp and stir for 12 h. The reaction mixture was poured into ice water and the aqueous layer was extracted four times with ethyl acetate and the combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. Two products were isolated by flash chromatography. (10% methanol-ethyl acetate) Yield 813.40 mg of the 4-nitro and 100 mg of the 6-nitro. 1H NMR (300 MHz, d6-DMSO): 4-nitro δ 7.76 (s, 1H), 8.19 (s, 1H), 8.98 (bs, 1H); 6-nitro δ 7.69 (d, J=9 Hz, 1H), 7.84 (d, J=9 Hz), 8.91 (bs, 1H).

Workup

  1. temperatureto slowly warm to room temp
  2. extractionthe aqueous layer was extracted four times with ethyl acetate
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customTwo products were isolated by flash chromatography

Sources & evidence

ORD record
ord-067ab89643124b93ad99a873ab4ee2b2
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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