Benzoyl chloride, 3-nitro- → Phthalimidine

HRID 1070542Notes

Reaction equation

HRID 1070542 reaction equation
O[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(Cl)Cl.C(N(CC)CC)C>[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 115064794-Hydroxy-2,3-dihydroisoindol-1-one

Product 1

HCID 10199PhthalimidineYield 28%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-hydroxy isoindolinone 27 (0.100 gm, 0.67 mmol) in methylene chloride (5 ml) and triethylamine (0.2 ml), was added m-nitrobenzoyl chloride (0.125 gm, 0.67 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 5 hr. After the usual workup, the resulting residue was purified by PTLC plate (solvent was 10% methanol-methylene chloride) to give 2,3-dihydro-1H-isoindol-1-one 32 (0.025 mg, 28%).

Workup

  1. customAfter the usual workup, the resulting residue was purified by PTLC plate (solvent was 10% methanol-methylene chloride)

Sources & evidence

ORD record
ord-22631155abf2444eb76367d6d4d83a8f
Source dataset
uspto-grants-2005_06
Patent number
US06903079B2

Reaction notes

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