Phthalic Anhydride → 2-(5-methyl-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione

HRID 38675Notes

Reaction equation

HRID 38675 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[C:8]1(=O)[O:13][C:11](=[O:12])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12>O1CCOCC1>[CH3:1][C:2]1[NH:6][N:5]=[C:4]([N:7]2[C:11](=[O:12])[C:10]3[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]2=[O:13])[CH:3]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 931461H-Pyrazol-3-amine, 5-methyl-

Product 1

HCID 37418032-(5-methyl-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dioneYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 100 mL round-bottom flask a mixture of 5-methyl-1H-pyrazol-3-amine (Aldrich, 500 mg, 5.15 mmol) and phthalic anhydride (ALDRICH) (1.07 g, 7.21 mmol) in 1,4-dioxane (30 mL) was stirred at reflux for 25 hours. Reaction was allowed to reach room temperature and the formed precipitate was filtered and washed with EtOH to afford 589 mg of the title compound as a yellowish solid. Filtrate was evaporated to dryness and after washing the residue with EtOH, an additional batch of 331 mg was obtained (total yield: 79%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 12.77 (br s, 1H), 7.87-7.98 (m, 4H), 6.09 (s, 1H), 2.28 (s, 3H). [ES+MS] m/z 228 (MH+).

Workup

  1. temperatureat reflux for 25 hours
  2. customReaction
  3. customto reach room temperature
  4. filtrationthe formed precipitate was filtered
  5. washwashed with EtOH

Sources & evidence

ORD record
ord-17b5c791b6974adda0cc3d0e9f864149
Source dataset
uspto-grants-2013_09
Patent number
US08524750B2

Reaction notes

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