N-Carbethoxyphthalimide → 2-[(3,4-Dimethoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 2301939Notes

Reaction equation

HRID 2301939 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH2:7].C(N1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])(OCC)=O>O1CCCC1.C(N(CC)CC)C>[C:19]1(=[O:28])[N:7]([CH2:6][C:5]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]12

Participants

5

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 79832Veratrylamine

Product 1

HCID 36674372-[(3,4-Dimethoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dioneYield 60%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3,4-dimethoxybenzylamine (0.836 grams, 5.00 mmol) and N-carbethoxyphthalimide (1.10 grams, 5.00 mmol) in 20 milliliters of tetrahydrofuran was added 1 drop of triethylamine and the mixture stirred overnight. After 24 hours at room temperature, the mixture was refluxed for 16 hours, then allowed to cool to room temperature without stirring. Crystals formed on cooling. The mixture was filtered, the solid dried in vacuo to afford 0.89 grams (60%) of 1-phthalimido-1-(3′,4′-dimethoxyphenyl)methane as small white needles: mp 160-161° C.; 1H NMR (CDCl3/TMS) δ7.8 (m, 2 H), 7.7 (m, 2 H), 7.03 (m, 2 H), 6.8 (m, 1 H), 4.78 (s, 2 H), 3.88 (s, 3 H, OCH3), 3.84 (s, 3 H, OCH3); 13C NMR (CDCl3/TMS) δ168.0, 148.9, 148.7, 133.9, 132.1, 129.0, 123.3, 121.3, 112.1, 111.1, 55.9, 41.4. Anal. Calcd for C17H15NO4. Theory C, 68.68; H, 5.09; N, 4.71. Found C, 68.49; H, 4.99; N, 4.67.

Workup

  1. waitAfter 24 hours at room temperature
  2. temperaturethe mixture was refluxed for 16 hours
  3. stirringwithout stirring
  4. customCrystals formed
  5. temperatureon cooling
  6. filtrationThe mixture was filtered
  7. customthe solid dried in vacuo

Sources & evidence

ORD record
ord-6917faa963c74223bc8125a2a0c749dd
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

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