Benzoyl chloride, 3-nitro- → Phthalimidine

HRID 1862087Notes

Reaction equation

HRID 1862087 reaction equation
N[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+](C1C=C(C=CC=1)C(Cl)=O)([O-])=O>C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[C:6]1(=[O:11])[C:7]2[C:3](=[CH:2][CH:10]=[CH:9][CH:8]=2)[CH2:4][NH:5]1

Participants

5

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 98555134-AMINOISOINDOLIN-1-ONE

Product 1

HCID 10199PhthalimidineYield 50.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The suspension of 2,3-dihydro-1H-isoindol-1-one 4 (0.100 gm, 0.61 mmol.) in ethyl acetate and aq. NaHCO3 solution, was added m-nitrobenzoyl chloride (0.15 mg, 0.81 mmol.) at room temperature. The reaction mixture was stirred at room temperature for 30 min, and solid separated was filtered and dried under vacuum to give 2,3-dihydro-1H-isoindol-1-one 25 (0.041 gm, 36%).

Workup

  1. customsolid separated
  2. filtrationwas filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-b0ada8de7c824ad6972e91428ff31e5f
Source dataset
uspto-grants-2003_03
Patent number
US06534651B2

Reaction notes

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