Phthalic Anhydride → HCID 178514958, compound

HRID 38674Notes

Reaction equation

HRID 38674 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[C:7]1(=O)[O:12][C:10](=[O:11])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12>O1CCOCC1>[NH:4]1[CH:5]=[CH:6][C:2]([N:1]2[C:10](=[O:11])[C:9]3[C:8](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]2=[O:12])=[N:3]1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 178418806HCID 178418806, compound

Product 1

HCID 178514958HCID 178514958, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 500 mL round-bottom flask a mixture of 3-aminopyrazole (Aldrich, 10 g, 120 mmol) and phthalic anhydride (Aldrich, 24.96 g, 168 mmol) in 1,4-dioxane (150 mL) was stirred at reflux for 17 hours. The reaction was allowed to reach room temperature and solvent was evaporated to dryness. Residue was washed with EtOH and a yellowish solid was filtered to afford 23.6 g (yield 92%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm: 13.09 (br s, 1H), 7.89-7.98 (m, 4H), 7.86 (br s, 1H), 6.36 (d, 1H). [ES+MS] m/z 214 (MH+).

Workup

  1. temperatureat reflux for 17 hours
  2. customto reach room temperature
  3. customsolvent was evaporated to dryness
  4. washResidue was washed with EtOH
  5. filtrationa yellowish solid was filtered

Sources & evidence

ORD record
ord-7f7f6d236f294044bd0244302e538dad
Source dataset
uspto-grants-2013_09
Patent number
US08524750B2

Reaction notes

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