Phthalic Anhydride → HCID 178514958, compound

HRID 522613Notes

Reaction equation

HRID 522613 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 92.5%

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 h. Solvent was evaporated to dryness. Residue was triturated with EtOH to afford (23.6 g, 111 mmol, 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 h
  2. customSolvent was evaporated to dryness
  3. customResidue was triturated with EtOH

Sources & evidence

ORD record
ord-7f8c0791bdd348c18dc917248c34b250
Source dataset
uspto-grants-2016_05
Patent number
US09334265B2

Reaction notes

Loading…