Ammonium Hydroxide → HCID 86749408, compound

Participants

Reaction Steps

A mixture of α-acetyl-β-(4-fluorophenyl)-δ-oxobenzenepentanoic acid, ethyl ester (6.12 gm) and hydroxylamine hydrochloride (3.61 gm, 52 mmol) in glacial HOAc (83 ml) was refluxed for 1 hour. The reaction was cooled to room temperature and poured into an ice cold solution of concentrated NH4OH (115 ml) in H2O (300 ml). The resulting mixture was extracted twice with Et2O and the combined Et2O layers were washed with brine, dried (Na2SO4), filtered and stripped to yield a dark gummy residue. The residue was chromatographed (Flash, Merck SiO2, 8% EtOAc in hexane) to give 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinecarboxylic acid, ethyl ester which was rechromatographed (8% EtOAc in hexane) to afford pyridine 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinecarboxylic acid, ethyl ester (1.652 gm, 24% from (E)-3-(4-fluorophenyl)-1-phenyl-2-propen-1-one) in >90% purity.

Provenance & Evidence