methyl 2-amino-4,6-dihydroxynicotinate synthesis

Yield:523992-26-9 64%

Reaction Conditions:

bis(acetylacetonate)nickel(II) in 1,4-dioxane; for 16 h;Reflux;

Steps:

116.116-1

Step 116-1 Cyanamide (1.4 g) and 1,4-dioxane (20 ml) were mixed, and dimethyl 1,3-acetonedicarboxylate (2.0 g) and nickel(II) acetylacetonate (0.30 g) were added. The mixture was heated under reflux for 16 hr. The mixture was cooled to room temperature, stirred for 1 hr and the resulting solid was collected by filtration. To the obtained solid was added methanol (6.0 ml) and the mixture was stirred at room temperature for 1.5 hr. The solid was collected by filtration to give the compound described in the above-mentioned scheme (1.4 g, 64%).¹H-NMR (DMSO-D₆) δ: 3.80 (s, 3H), 4.92 (s, 1H), 7.20 (s, 2H), 10.29 (s, 1H), 11.51 (s, 1H).

References:

US2011/77267,2011,A1 Location in patent:Page/Page column 48