Phthalimide → 2-(3,5-Dimethylphenyl)-1H-isoindole-1,3(2H)-dione

HRID 1883339Notes

Reaction equation

HRID 1883339 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C([O-])([O-])=O.[K+].[K+].[C@@H]1(N)CCCC[C@H]1N.CCCCCCCCCCCC.I[C:39]1[CH:40]=[C:41]([CH3:46])[CH:42]=[C:43]([CH3:45])[CH:44]=1>[Cu]I.O1CCOCC1>[CH3:46][C:41]1[CH:40]=[C:39]([N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[CH:44]=[C:43]([CH3:45])[CH:42]=1

Participants

8

Reactant 5

HCID 6809PhthalimideHCID 8182DodecaneHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 6937342-(3,5-Dimethylphenyl)-1H-isoindole-1,3(2H)-dioneYield 13%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

An oven-dried resealable Schlenk tube was charged with CuI (200 mg, 1.05 mmol), phthalimide (185 mg, 1.26 mmol), K2CO3 (290 mg, 2.10 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (130 μL, 1.06 mmol), dodecane (235 μL), 5-iodo-m-xylene (150 μL, 1.04 mmol) and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 23 h. The resulting brown suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 3:1; 15 mL fractions). Fractions 8-11 provided 34 mg (13% yield) of the product as a tan solid. The 1H NMR spectrum was in accord with that reported by Hashimoto et al. Shibata, Y.; Sasaki, K.; Hashimoto, Y.; Iwasaki, S. Chem. Pharm. Bull. 1996, 44, 156.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed
  3. temperatureThe resulting brown suspension was cooled to room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 3:1; 15 mL fractions)

Sources & evidence

ORD record
ord-02c9792254454f1e8b30a54c3b99b10e
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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