Ammonia → HCID 178469844, compound

Participants

Reaction Conditions

Reaction Steps

3-Oxo-pentanedioic acid (101 g, 0.5 mmol), diethyl ester, triethyl orthoformate (81.4 g, 0.55 mol) and acetic anhydride (102 g, 1 mol) were combined and heated to 120° C. for 2 h. The resulting mixture was cooled to RT and dissolved in DCM (1000 mL). After further cooling to 0° C., ammonia (30%, 80 mL) was added and the reaction mixture was allowed to warm to RT overnight. The product was extracted with water (2×1000 mL). Then the aqueous layer was acidified to pH 5 with cone HCl. The precipitate was collected by filtration to afford ethyl 4,6-dihydroxynicotinate (60.0 g, 60% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.99 (s, 1H), 5.58 (s, 1 H), 4.23 (q, J=6.8, 14.0 Hz, 2 H), 1.25 (t, J=7.2 Hz, 3 H). MS (ESI) m/z: 184.1 (M+H+).

Provenance & Evidence