Water → 7-Hydroxy-2-methyl-6-nitro-2,3-dihydroisoindol-1-one

HRID 1528169Notes

Reaction equation

HRID 1528169 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2.S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19].O.[Cl-].[Na+]>S(=O)(=O)(O)O>[OH:1][C:2]1[C:3]([N+:18]([O-:20])=[O:19])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 585225447-hydroxy-2-methyl-2,3-dihydro-1H-isoindol-1-oneHCID 71777668Sulfuric acid, mixt. with nitric acid

Product 1

HCID 895250337-Hydroxy-2-methyl-6-nitro-2,3-dihydroisoindol-1-oneYield 11%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-20 °C

Procedure

2.49 g (91.5 mmol) of 7-hydroxy-2-methyl-2,3-dihydroisoindol-1-one were dissolved at 0° C. in 6 ml of concentrated sulfuric acid. The reaction medium was cooled to −20° C. and 1.8 ml of a 4/5 mixture of concentrated sulfuric acid/nitric acid at 70% were added. After 10 minutes, the reaction medium was hydrolyzed with water. Sodium chloride was added and the medium was extracted twice with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a C18 column twice (40 g prepacked column, water/acetonitrile gradient). 350 mg of product were obtained in the form of a yellow solid. Yield=11%.

Workup

  1. additionwere added
  2. extractionthe medium was extracted twice with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on a C18 column twice (40 g prepacked column, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-f9957a64544a4609b16007bda423a522
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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