Nitric Acid → 4-Bromo-7-nitro-2,3-dihydro-isoindol-1-one

HRID 1247447Notes

Reaction equation

HRID 1247447 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 219075094-Bromoisoindolin-1-one

Product 1

HCID 219075574-Bromo-7-nitro-2,3-dihydro-isoindol-1-oneYield 88.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of Example 1C (5 g, 23.6 mmol) in 10 mL sulfuric acid was treated with a solution of concentrated nitric acid (1.55 mL, 24.7 mmol) in 10 mL sulfuric acid via addition funnel. The resulting mixture was stirred at 0° C. for 1 hour, warmed to room temperature, stirred overnight, poured over ice, and filtered. The filter cake was washed with water and diethyl ether and then dried to give 5.39 g of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 4.39 (s, 2H); 7.88 (d, J=8.1 Hz, 1H); 8.05 (d, J=8.5 Hz, 1H); 9.17 (s, 1H).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. additionpoured over ice
  4. filtrationfiltered
  5. washThe filter cake was washed with water and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-a487b3064f77409c929c07e10e806b0b
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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