Nitric Acid → 4-Bromo-2-methyl-7-nitroisoindolin-1-one

HRID 511242Notes

Reaction equation

HRID 511242 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH3:12])[C:6]2=[O:11].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N+:13]([O-:15])=[O:14])=[C:7]2[C:3]=1[CH2:4][N:5]([CH3:12])[C:6]2=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 219075344-Bromo-2-methylisoindolin-1-one

Product 1

HCID 534078944-Bromo-2-methyl-7-nitroisoindolin-1-oneYield 74%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold suspension of 4-bromo-2-methyl-2,3-dihydroisoindol-1-one (60 g, 265 mmol) in concentrated sulfuric acid (60 mL) was added pre-cooled mixture of conc. nitric acid (12.5 mL, 265 mmol) and conc. sulfuric acid (60 mL) over 20 min. The reaction mixture was stirred for 30 min at 0° C. and 2 h at room temperature. The reaction mixture was poured over ice-water mixture (300 mL). The precipitate was filtered, washed with water (3×100 mL) and suspended in isopropanol (200 mL). The slurry was heated on steam bath and cooled. The solid was filtered and dried in air to give 53 g (74%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ 3.22 (s, 3H), 4.36 (s, 2H), 7.67 (d, J=8.4 Hz, 1H), 7.78 (d, J=8.4 Hz, 1H).

Workup

  1. additionwas added
  2. temperaturepre-cooled
  3. filtrationThe precipitate was filtered
  4. washwashed with water (3×100 mL)
  5. temperatureThe slurry was heated on steam bath
  6. temperaturecooled
  7. filtrationThe solid was filtered
  8. customdried in air

Sources & evidence

ORD record
ord-30be0a000ce94ce7818a168c2bfa2920
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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