Phthalimide potassium salt → HCID 66597897, compound

HRID 1518647Notes

Reaction equation

HRID 1518647 reaction equation
BrC[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([N+:16]([O-:18])=[O:17])[CH:5]=1.[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.[K]>CN(C)C=O>[N+:16]([C:6]1[CH:5]=[C:4]([CH2:3][N:23]2[C:19](=[O:29])[C:20]3[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:22]2=[O:24])[CH:9]=[CH:8][C:7]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 66597098HCID 66597098, compound

Product 1

HCID 66597897HCID 66597897, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

4-(Bromoethyl)-2-nitro-1-phenylbenzene (584.3 mg, 2.0 mmol) and potassium phthalimide (555.0 mg, 3.0 mmol) were dissolved in N,N-dimethylformamide (8 mL) and the mixture was stirred at 110° C. for 3 hours. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain 2-[(3-nitro-4-phenylphenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione (600.8 mg).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-bed79dfa97444061ad388a3127d12d21
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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