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

HRID 1760566Notes

Reaction equation

HRID 1760566 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) δ 7.8 (m, 2H), 7.7 (m, 2H), 7.03 (m, 2H), 6.8 (m, 1H), 4.78 (s, 2H), 3.88 (s, 3H, OCH3), 3.84 (s, 3H, OCH3); 13C NMR (CDCl3/TMS) δ 168.0, 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-fc4c2675576b40328af1a36056b46682
Source dataset
uspto-grants-2005_01
Patent number
US06844359B2

Reaction notes

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