Benzyl Bromide → HCID 14856060, compound

Participants

Reaction Steps

12.96 g of the title compound of Example 1, 5.52 g potassium carbonate and 10.40 g benzylbromide were dissolved in 200 ml DMF and kept at 80°-90° C. for 18 hours. The solvent was then distilled off in vacuo and the oil residue dissolved in 100 ml ethyl acetate and 100 ml water. The organic layer was separated and washed again with 50 ml water. The solvent of the dried organic phase was then stripped off to afford an oily residue (18 g). The oil was dissolved in 30 ml ethyl acetate/cyclohexane (1:1). 4.1 g 3-bromo-1,4-dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)- 2-pyridinecarboxylic acid, phenylmethyl ester crystallized from the solution. The filtrate was chromatographed on silica gel using ethylacetate/cyclohexane (1:1) as eluent. Fractions 33-35 contained 4 g pure title compound M.P.=98°-100° C.; another 1.9 g title compound with 10% 3-Bromo-1,4-dihydro-4-oxo-5 -(phenylmethoxy)-1-(phenylmethyl)-2-pyridinecarboxylic acid, phenylmethyl ester were obtained from fractions 57-104.

Provenance & Evidence