Formamide → 5-Methoxy-1H-isoindole-1,3(2H)-dione

HRID 41397Notes

Reaction equation

HRID 41397 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=O)[O:9][C:7](=[O:8])[C:6]2=[CH:12][CH:13]=1.C([NH2:16])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[O:9])[NH:16][C:7](=[O:8])[C:6]2=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 6397485-Methoxy-1,3-dihydro-2-benzofuran-1,3-dione

Product 1

HCID 131527195-Methoxy-1H-isoindole-1,3(2H)-dioneYield 77%

Procedure

A mixture of 4-methoxyphthalic anhydride (27.8 g, 0.16 mol) and formamide (175 ml) was stirred and held at 210° C. for 5 hours and was then allowed to cool to room temperature overnight. The solid material was filtered off, washed sequentially with water (100 ml), 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford 4-methoxyphthalimide (21.3 g, 77%) as a pale yellow solid. 1H NMR (DMSO-d6) 11.15 (1H, br s), 7.74 (1H, d), 7.33-7.28 (2H, m), 3.92 (3H, s).

Workup

  1. filtrationThe solid material was filtered off
  2. washwashed sequentially with water (100 ml), 50% aqueous acetone (50 ml) and diethyl ether (200 ml)
  3. customsucked dry under reduced pressure

Sources & evidence

ORD record
ord-27f071f83ac0413aba0618360d7523cd
Source dataset
uspto-grants-2013_09
Patent number
US08530469B2

Reaction notes

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