Sodium Bicarbonate → 6-Oxopiperidine-3-carboxylic acid

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Reaction Steps

To a suspension of 10.0 g of 6-hydroxynicotinic acid in 200 ml water were added 6.5 g of sodium bicarbonate. The resulting solution was subjected to 500 psig hydrogen at 100° C. for 12 hours in the presence of 2.5 g ruthenium on alumina. The catalyst was removed by filtration. The filtrate was acidified to pH 4 with 6N HCl and evaporated to a colorless solid (~15 g). The solid was treated with 40 ml methanol and filtered to remove most of the sodium chloride. The filtrate was evaporated to give 7.5 g of the title compound: MS m/z 143 (M+); 300-MHz 1H NMR (DMSO-d6) δ1.62-1.77 (m, 1H), 1.83-1.97 (m, 1H), 2.00-2.21 (m, 2H), 2.23-2.35 (m, 1H), 3.21 (d, J=8 Hz, 2H), 7, 28 (s, 1H).

Provenance & Evidence