Hydrochloric Acid → HCID 10446445, compound

Participants

Reaction Conditions

Reaction Steps

2-Acetylpyridine (10.0 g, 0.0825 mole) was added to 50° C. solution of sodium cyanide (4.0 g, 0.0825 mole) ammonium chloride (4.9 g, 0.0908 mole), and ammonium hydroxide (2.9 g, 0.0825 mole ) in water (22 mL) and methanol (15 mL). The resulting mixture was stirred at 50° C. overnight. The mixture was cooled and concentrated under reduced pressure. The residue was dissolved in methylene chloride (40 mL) and washed with water (10 mL) and dried over MgSo4. Filtration and concentration gave a dark red oil which was dissolved in methanol and treated with saturated ethereal HCl. Concentration yielded a low melting solid which was dissolved in tetrahydrofurna (50 mL) and treated sequentially with triethylamine (13.7 g, 0.135 mole) and p-anisoyl chloride (8.4 g, 0.0495 mole) dropwise. The solution was stirred 3 hours at room temperature then diluted with ether (100 mL) and washed with 2M HCl, 1M NaOH, saturated NaCl, and dried over MgSo4. Filtration and concentration of the solvent in vacuo provided a solid which was recrystalized from ethyl acetate/hexane to give 5.2 g of N-[-1-cyano-1-(2-pyridinyl)ethyl]-4-methoxybenzamide, mp 173° C.

Provenance & Evidence