Acetic Acid → 3-Acetamido-2-phenylpyrazolo[1,5-a]pyridine

Reaction equation

[N:1]([C:3]1[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12)=O.C(=O)(O)[O-].[Na+].[C:23](O)(=[O:25])[CH3:24]>[Zn]>[C:23]([NH:1][C:3]1[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12)(=[O:25])[CH3:24]

Participants

Procedure

A mixture of 3-nitroso-2-phenylpyrazolo[1,5-a]pyridine (0.81 g) and zinc powder (0.95 g) in acetic acid (10 ml) was heated under reflux for 2.5 hours. The reaction mixture was poured onto ice-water (100 ml) and neutralized with saturated aqueous sodium bicarbonate solution. Resultant precipitates were collected by filtration, washed with water, and recrystallized from ethyl acetate to give crystals of 3-acetamido-2-phenylpyrazolo[1,5-a]pyridine (304 mg).