Azobisisobutyronitrile → 5-nitro-2,3-dihydro-1H-isoindol-1-one

HRID 1039086Notes

Reaction equation

HRID 1039086 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.[CH2:13]1[C:18](=O)[N:17](Br)[C:15](=[O:16])[CH2:14]1.CC1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28]C=1C(OC)=O>C(Cl)(Cl)(Cl)Cl>[N+:32]([C:30]1[CH:31]=[C:13]2[C:14](=[CH:28][CH:29]=1)[C:15](=[O:16])[NH:17][CH2:18]2)([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 15088700Methyl 2-methyl-4-nitrobenzoate

Product 1

HCID 140056255-nitro-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

AIBN (84 mg, 0.51), NBS (1.1 gram, 6.4 mmol), and the methyl 2-methyl-4-nitrobenzoate (1 g, 5.1 mmol) from step 1 of this example were suspended in CCl4 and the mixture heated under N2 at 79 C overnight. The solution was filtered, and concentrated in vacuum. The residue was dissolved in 7 N ammonia in methanol (15 ml) and the solution stirred for 2 hours at RT. The mixture was concentrated in vacuum. and the resulting solid suspended in EtOAc (21.5 ml), heated at 80° C. for 30 minutes with stirring, cooled RT and aged at −20° C. for the 3 days. The solid was isolated by filtration to give the titled compound.

Workup

  1. temperaturethe mixture heated under N2 at 79 C overnight
  2. filtrationThe solution was filtered
  3. concentrationconcentrated in vacuum
  4. dissolutionThe residue was dissolved in 7 N ammonia in methanol (15 ml)
  5. concentrationThe mixture was concentrated in vacuum
  6. temperatureheated at 80° C. for 30 minutes
  7. stirringwith stirring
  8. temperaturecooled RT
  9. customaged at −20° C. for the 3 days
  10. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-d66f961f10fb4003b82b9767ca781fe3
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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