Methyl iodide → 1H-Isoindole-1,3(2H)-dione, 2-methyl-4-nitro-

HRID 1872701Notes

Reaction equation

HRID 1872701 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([NH:9][C:10](=[O:11])[C:5]=12)=[O:8])([O-:3])=[O:2].[H-].[Na+].I[CH3:18]>CN(C)C=O>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([N:9]([CH3:18])[C:10](=[O:11])[C:5]=12)=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 117793-NitrophthalimideHCID 24758Sodium hydride

Product 1

HCID 757721H-Isoindole-1,3(2H)-dione, 2-methyl-4-nitro-Yield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-nitrophthalimide (Aldrich)(1.78 g, 0.01 mol) in dry N,N-dimethylformamide (20 ml) was added dropwise to a stirred suspension of sodium hydride (0.36 g of an 80% dispersion in oil; 0.012 mol) in dry N,N-dimethylformamide (10 ml) under argon. The mixture was stirred at room temperature for 30 min and then treated with iodomethane (0.75 ml, 0.012 mol). After stirring overnight the reaction was poured into ice-water and extracted with dichloromethane (4×50 ml). The combined extracts were washed with water followed by brine, then dried over sodium sulfate and concentrated in vacuo. The residue was treated with water, and the resulting precipithate was removed by filtration and washed with water. After drying in a vacuum dessicator over silica gel the title compound was obtained as a yellow solid (1.64 g).

Workup

  1. stirringAfter stirring overnight the reaction
  2. extractionextracted with dichloromethane (4×50 ml)
  3. washThe combined extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue was treated with water
  7. customthe resulting precipithate was removed by filtration
  8. washwashed with water
  9. dry with materialAfter drying in a vacuum dessicator over silica gel the title compound

Sources & evidence

ORD record
ord-0e7c176dc65c4e709cea0e2e567004fc
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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