Formamide → 5-Fluoroisoindoline-1,3-dione

HRID 225685Notes

Reaction equation

HRID 225685 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=O)[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.C([NH2:15])=O>>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][CH:12]=1)[C:6](=[O:7])[NH:15][C:9]2=[O:8]

Participants

3

Reactant 2

HCID 713FormamideHCID 675721,3-Isobenzofurandione, 5-fluoro-

Product 1

HCID 108990385-Fluoroisoindoline-1,3-dioneYield 100%

Conditions

Temperature
200 °C

Procedure

A mixture of 144 mmol 4-fluorophthalic anhydride and 1.16 mol formamide was heated at 200° C. for 2 h. The reaction mixture was poured onto ice-water and the resulting crystals collected by filtration and dried in vacuo to afford the title compound as a yellow solid (100% yield). MS (m/e): 164.4 ([M−H]−, 100%).

Workup

  1. additionThe reaction mixture was poured onto ice-water
  2. filtrationthe resulting crystals collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-4d1aa1d4c0e743ae80a7cbddc416b708
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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