Acetic Acid → HCID 53915788, compound

Reaction equation

C(O)(=O)C.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[N:20]O)[CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:6]=1>C(O)C.[Zn]>[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([NH2:20])[CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH:6]=1

Participants

Procedure

Acetic acid (16 mL) was added to a suspension of 1-(3-pyridyl)-3-(4-oxanyl)propan-1-one oxime (1.60 g, 6.83 mmol) in 95% ethanol (40 mL) over a period of 15 min. Zinc dust (12 g, 180 mmol) was added and the reaction mixture was stirred at ambient temperature for 4 h. The reaction mixture was filtered through a Celite plug, which was then washed with ethanol (50 mL). The combined filtrates were concentrated by rotary evaporation. The solid residue was made basic by addition of 50% aqueous NaOH (with ice bath cooling), saturated with solid NaCl and extracted with chloroform (5×30 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated by rotary evaporation to give pure product as a colorless viscous liquid (1.40 g, 82% yield).