Formamide → 4-Methoxyisoindoline-1,3-dione

HRID 2412220Notes

Reaction equation

HRID 2412220 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 was 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 was washed sequentially with 50% aqueous acetone (50 ml) and diethyl ether (200 ml)
  3. customsucked dry under reduced pressure

Sources & evidence

ORD record
ord-1e8b8102f25c486ba86b0d89b4afc78c
Source dataset
uspto-grants-2014_08
Patent number
US08816087B2

Reaction notes

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