Phthalimidine → HCID 57885105, compound

HRID 1818768Notes

Reaction equation

HRID 1818768 reaction equation
[H-].[Na+].[C:3]1(=[O:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][NH:4]1.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:15]>C1COCC1>[N+:23]([C:20]1[CH:19]=[CH:18][C:17]([O:16][C:14](=[O:15])[O:12][C:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][N:4]=2)=[CH:22][CH:21]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 10199PhthalimidineHCID 24758Sodium hydrideHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 57885105HCID 57885105, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (18 mg, 60% dispension in mineral oil, 0.454 mmol) in THF (10 mL), 2,3-dihydro-isoindol-1-one (55 mg, 0.413 mmol) was added. The reaction mixture was stirred at room temperature for 1 hours. The p-nitrophenyl chloroformate (91.5 mg, 0.454 mmol) was added and the reaction mixture was stirred at room temperature for overnight. Solvent was concentrated and the residue was washed with methanol. White solid was collected as pure product carbonic acid 3H-isoindol-1-yl ester 4-nitro-phenyl ester (37 mg, 30% yield).

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for overnight
  3. concentrationSolvent was concentrated
  4. washthe residue was washed with methanol

Sources & evidence

ORD record
ord-6ee17fde130a40a7aa21cc5add0ae6d4
Source dataset
uspto-grants-2009_10
Patent number
US07601686B2

Reaction notes

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