Methylamine → HCID 54151562, compound

Participants

Reaction Steps

A mixture of 10.0 g of 2-methyl-4-(1-oxido-3-pyridyl)-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylic acid ethyl ester and 100 ml of a 33% solution of methylamine in ethanol is heated at 90° in a sealed tube for 16 hours. The reaction mixture is concentrated to dryness by evaporation under reduced pressure and the residue is partitioned between methylene chloride and a 2N aqueous sodium carbonate solution. The organic phase is removed, washed with water, dried and concentrated by evaporation under reduced pressure. The residue is chromatographed over silica gel and eluted with ethyl acetate. The uniform fractions ascertained by means of a thin layer chromatograph are concentrated to dryness by evaporation under reduced pressure and the residue is recrystallised from a mixture of isopropanol and petroleum ether to yield 6-hydroxymethyl-2-methyl-5-methylaminocarbonyl-4-(1-oxido-3-pyridyl)-1,4-dihydropyridine-3-carboxylic acid ethyl ester melting at 197°.

Provenance & Evidence