Formamide → 4-Methoxyisoindoline-1,3-dione

HRID 2355752Notes

Reaction equation

HRID 2355752 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:6]([O:8][C:9](=O)[C:4]=12)=[O:7].C([NH2:16])=O>O>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:5]2[C:6]([NH:16][C:9](=[O:8])[C:4]=12)=[O:7]

Participants

4

Reactant 2

HCID 713FormamideHCID 2911934-Methoxy-1,3-dihydro-2-benzofuran-1,3-dione

Product 1

HCID 166382284-Methoxyisoindoline-1,3-dioneYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-methoxyphthalic anhydride (24.0 g, 134.8 mmol) and formamide (120 ml) was stirred and held at 210° C. for 5 hours and was then allowed to cool to room temperature overnight. Water (100 ml) was added and the solid material filtered off under reduced pressure. The crude product washed sequentially with 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford 3-methoxyphthalimide (8.95 g, 37%) as an off-white solid. 1H NMR (DMSO-d6) 11.08 (1H, br s), 7.78 (1H, dd), 7.45 (1H, d), 7.36 (1H, d), 3.93 (3H, s). MS: [M+H]+ 178.

Workup

  1. filtrationthe solid material filtered off under reduced pressure
  2. washThe crude product washed sequentially with 50% aqueous acetone (50 ml) and diethyl ether (200 ml)
  3. customsucked dry under reduced pressure

Sources & evidence

ORD record
ord-1429fd657fad4e9cace48cd61ea19a3e
Source dataset
uspto-grants-2010_07
Patent number
US07754725B2

Reaction notes

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