Sodium Hydroxide → 2-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)acetic acid

Participants

Reaction Steps

To methyl 2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)acetate (5.50 g, 25.1 mmol) in methanol (100 mL) was added aqueous 1N NaOH (50.2 mmol). The reaction was stirred at room temperature for 1 hour. The reaction mixture was concentrated and water (200 mL) was added. The aqueous solution was washed with 2-methyl-THF (2×200 mL). The aqueous layer was adjusted to pH˜5 and was concentrated. The resulting solids were suspended in chloroform (200 mL) and the mixture was heated to reflux with stirring. The mixture was heated at reflux for 10 minutes and was filtered while hot. The resulting filtrate was concentrated in vacuo to afford 2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)acetic acid (SM-1aj, 2.5 g, 57%). MS (ES+) 196.2 (M+H)+. 1H NMR (CDCl3) δ 3.23 (s, 2H), 4.14 (s, 2H), 4.30 (s, 2H), 6.77 (d, 1H), 7.08 (d, 1H).

Provenance & Evidence