2-Morpholinoethanol → HCID 71060751, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloronicotinic acid (Aldrich, 1.00 g, 6.35 mmol) and t-BuOK (1.42 g, 12.7 mmol) in DMSO (10.0 mL) was added 2-morpholinoethanol (1.5 mL, 12.7 mmol) at room temperature. The reaction mixture was then heated at 95° C. for 16 h. Additional t-BuOK (1.42 g, 12.7 mmol), 2-morpholinoethanol (1.54 mL, 12.7 mmol) and DMSO (10.0 mL) were added, and the reaction mixture was heated at 95° C. for another 24 h. The reaction mixture was then cooled to room temperature, poured into ice cold 4N aq. HCl solution and extracted with EtOAc (3×). The aqueous layer was concentrated in vacuo to near dryness and purified using preparative HPLC to give the title compound (150 mg, 9%) as a white solid after lyophilization. 1H NMR (DMSO-d6) δ 13.1 (br s, 1H), 8.74 (d, J=1.8 Hz, 1H), 8.21 (dd, J=8.6, 2.2 Hz, 1H), 6.98 (d, J=8.6 Hz, 1H), 4.69 (br s, 4H), 3.96 (br s, 2H), 3.75-3.70 (m, 2H), 3.19 (br s, 4H); MS(ESI+) m/z 253.2 (M+H)+.

Provenance & Evidence