Sodium Hydroxide → HCID 68773802, compound

Participants

Reaction Conditions

Reaction Steps

The above-prepared nitrile (500 mg, 2.9 mmol) was dissolved in a mixture of H2SO4 (conc. 4 ml) and H2O (1 ml). The mixture was heated at 120° C. for 16 h. It was then cooled to 90° C. and NaNO2 (1.4 g, 20 mmol) was added in small portions over 10 min. The reaction was heated at 90° C. for and additional 1 h and then cooled to rt and poured into an ice-water mixture (˜20 ml). The chilled mixture was basified to PH=12 using 10N NaOH. The aqueous mixture was then washed with CH2Cl2 (15 ml×2) to remove impurities. It was then acidified to PH=2. After being concentrated under high vacuum to dryness, the residue was extracted with CH2Cl2/CH3OH (4/1, 30 ml×3). The combined extracts were concentrated to give 5,7-dimethyl-imidazo[1,2-a]pyridine-6-carboxylic acid (500 mg, 90% containing impurities) as a beige solid. 1H NMR (CDCl3) δ 2.56 (s, 3H), 2.83 (s, 3H), 7.74 (s, 1H), 8.08 (d, 1H, J=1.8 Hz), 8.22 (d, 1H, J=1.8 Hz).

Provenance & Evidence