Acetic Acid → HCID 15282632, compound

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-pyridine (23.8 g, 0.25 mol) and solid sodium hydroxide (NaOH, 10.0 g, 0.25 mol) are dissolved in water (100 mL) and the solution is heated to 90° C. To this hot stirred solution, a 37% aqueous solution of formaldehyde (85mL) is added dropwise over a period of eight (8) hours. After the addition of formaldehyde is completed, the mixture is stirred at 90° C. for an additional 90 minutes. Heating is then discontinued and the mixture is chilled at 0° C., neutralized by the addition of 15 mL of acetic acid (CH3COOH), and evaporated to dryness in a rotary evaporator under reduced pressure. The residue is taken up in 200 mL of dimethylformamide, filtered to remove any undissolved solid which is discarded, and acidified by the addition of concentrated aqueous hydrochloric acid (25 mL). The acidified solution is evaporated to dryness in a rotary evaporator under reduced pressure and the residue is dissolved in methanol (150 mL), clarified with activated charcoal, and filtered. The resulting clear solution is again evaporated to dryness in a rotary evaporator under reduced pressure. Recrystallization of the oily residue, first from n-propanol and then from methanol-acetone, yields the desired product (yields, 35%) as a cream-colored solid, m.p. 144° C, having the correct analytical and spectral (IR and NMR) properties.

Provenance & Evidence