Formamide → 4-Methoxyisoindoline-1,3-dione

HRID 424115

Reaction equation

HRID 424115 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-72be81a7801c49fd89559a9f8c568ae4
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Linked notes

Loading…