2-Furancarboxylic acid → 5-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furoic acid

HRID 397700

Reaction equation

HRID 397700 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].O[CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21]>S(=O)(=O)(O)O>[O:21]=[C:12]1[C:13]2[C:14](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:16])[N:11]1[CH2:10][C:5]1[O:1][C:2]([C:6]([OH:8])=[O:7])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 69192-Furancarboxylic acidHCID 8354N-(hydroxymethyl)phthalimide

Product 1

HCID 230007015-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furoic acidYield 52.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-Furoic acid (10.0 g) was dissolved in cold concentrated sulphuric acid (50 ml). The mixture was then added to N-hydroxy methylphthalimide (12.0 g) and the reaction mixture allowed to stand for 18 hrs at room temperature. The mixture was then poured into ice and the product extracted with dichloromethane, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was triturated with diethyl ether and recrystallised from methanol to afford 5-[(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)methyl]-2-furoic acid (9.70 g) as a brown solid.

Workup

  1. additionThe mixture was then poured into ice
  2. extractionthe product extracted with dichloromethane
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed under reduced pressure
  5. customThe crude product was triturated with diethyl ether
  6. customrecrystallised from methanol

Sources & evidence

ORD record
ord-95eaf846f280435abc9809bec6e71199
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Linked notes

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