3-(6-OXO-1,6-DIHYDROPYRIDAZIN-3-YL)PROPANOIC ACID synthesis

Yield: 91.4%

Reaction Conditions:

with LiOH in tetrahydrofuran;water

Steps:

46 3-oxo-2,3,-Dihydropyridazin-6-yl-propionic Acid
Example 46 3-oxo-2,3,-Dihydropyridazin-6-yl-propionic Acid To a solution of Ethyl (3-oxo-2,3,-dihydropyridazin-6-yl)-propionate (3.00 mmol, 589 mg) in THF was added LiOH (2M, aqueous) (7.50 mL). The solution was stirred at rt. for 15 minutes, additional water (25 mL) was added and the THF removed in vacuo. The pH of the aqueous phase was adjusted to 3.0 by addition of HCl (2M, aqueous) and the solid material filtered off and washed with water (2*3 mL). The solid was dried in vacuo to yield the desired product (461 mg, 91.4%) as a colorless powder. ¹H NMR (CDCl₃): δ 11.62 (s br, 1H, NH), 7.18 (d, J=9.7 Hz, 1H, arom.), 7.88 (d, J=9.7 Hz, 1H, arom.), 4.11 (q, J=7.1 Hz, 2H, CH₂), 2.90 (t, J=7.0 Hz, 2H, CH₂), 2.64 (t, J=7.0 Hz, 2H, CH₂), 1.25 (t, J=7.1 Hz, 3H, CH₃). FAB⁺MS: 169.0611 (M+H⁺, calc. for C₉H₁₂N₂O₃+H⁺169.0613).

References:

Nielsen, Peter US6632919, 2003, B1