Azobisisobutyronitrile → 2-Methyl-5-nitroisoindolin-1-one

HRID 1039089Notes

Reaction equation

HRID 1039089 reaction equation
CC(N=NC(C#N)(C)C)([C:4]#[N:5])C.C1C(=O)N(Br)C(=O)C1.[CH3:21][C:22]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:23]=1[C:24](OC)=[O:25]>C(Cl)(Cl)(Cl)Cl>[CH3:4][N:5]1[CH2:21][C:22]2[C:23](=[CH:28][CH:29]=[C:30]([N+:32]([O-:34])=[O:33])[CH:31]=2)[C:24]1=[O:25]

Participants

5

Reactant 3

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

Product 1

HCID 592252992-Methyl-5-nitroisoindolin-1-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
79 °C

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, as prepared in Step 1, Example 44) were suspended in CCl4 (12.8 ml), the vessel evacuated and backfilled with N2 (2×) and the mixture heated under N2 at 79° C. overnight. The solution was filtered, and concentrated in vacuum. One third of the crude material was dissolved in 2 N methylamine in methanol (18 ml), 2N methylamine in THF added (18 ml) and the solution stirred for 2 hours at RT. The volatiles were removed in vacuum and the product was purified by chromatography on SiO2 eluting with 10% acetone:DCM to give the titled compound.

Workup

  1. customthe vessel evacuated
  2. filtrationThe solution was filtered
  3. concentrationconcentrated in vacuum
  4. dissolutionOne third of the crude material was dissolved in 2 N methylamine in methanol (18 ml)
  5. addition2N methylamine in THF added (18 ml)
  6. customThe volatiles were removed in vacuum
  7. customthe product was purified by chromatography on SiO2 eluting with 10% acetone

Sources & evidence

ORD record
ord-91ac261f03a248548ab47fb554f4e77d
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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