Formamide → 4-Fluoro-1H-isoindole-1,3(2H)-dione

HRID 877233Notes

Reaction equation

HRID 877233 reaction equation
[F:1][C:2]1[C:10]2[C:9](=[O:11])[O:8][C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([NH2:15])=O>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[NH:15][C:7]2=[O:8]

Participants

3

Reactant 2

HCID 713FormamideHCID 695513-Fluorophthalic anhydride

Product 1

HCID 220646324-Fluoro-1H-isoindole-1,3(2H)-dione

Procedure

Under argon, 10.0 g (60.2 mmol) of 4-fluoro-2-benzofuran-1,3-dione were stirred at 130° C. in 50 ml of formamide for 1 h. The cooled reaction mixture was then added to ice-water. A solid precipitated out. This solid was filtered off with suction and washed with water. The product was dried under high vacuum. This gave 8.3 g (83% of theory) of the target compound.

Workup

  1. customThe cooled reaction mixture
  2. customA solid precipitated out
  3. filtrationThis solid was filtered off with suction
  4. washwashed with water
  5. customThe product was dried under high vacuum

Sources & evidence

ORD record
ord-b2fca52572a64127951fa996562bcee7
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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