2,3-dimethylbenzamide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-pyridin-2-ylpiperazine (16 mg, 0.1 mmol, Aldrich), paraformaldehyde (30 mg, 1 mmol), 2,3-dimethylbenzamide (75 mg, 0.5 mmol, Lancaster), and 42 mg of potassium carbonate (0.3 mmol) in 2 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 29 mg (88%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 2.20 (s, 3H), 2.24 (s, 3H), 2.61 (t, J=4 Hz, 4H), 3.48 (t, J=4 Hz, 4.15 (d, J=5 Hz, 1H), 6.62 (t, J=5 Hz, 1H), 6.81 (d, J=6 Hz, 1H), 7.03 (m, 2H), 7.21 (t, J=5 Hz, 1H), 7.51 (t, J=6 Hz, 1H), 8.12 (d, J=5 Hz, 1H), 8.52 (t, J=5 Hz, 1H); MS (ESI/APCI−) m/e 323 (M−H)+. was heated to reflux under nitrogen overnight filtered the solvent was removed The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-pyridin-2-ylpiperazine (16 mg, 0.1 mmol, Aldrich), paraformaldehyde (30 mg, 1 mmol), 2,3-dimethylbenzamide (75 mg, 0.5 mmol, Lancaster), and 42 mg of potassium carbonate (0.3 mmol) in 2 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 29 mg (88%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 2.20 (s, 3H), 2.24 (s, 3H), 2.61 (t, J=4 Hz, 4H), 3.48 (t, J=4 Hz, 4.15 (d, J=5 Hz, 1H), 6.62 (t, J=5 Hz, 1H), 6.81 (d, J=6 Hz, 1H), 7.03 (m, 2H), 7.21 (t, J=5 Hz, 1H), 7.51 (t, J=6 Hz, 1H), 8.12 (d, J=5 Hz, 1H), 8.52 (t, J=5 Hz, 1H); MS (ESI/APCI−) m/e 323 (M−H)+. was heated to reflux under nitrogen overnight filtered the solvent was removed The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Heated at 70° for 30 min. a mixture containing 23.3 g (0.16 mole) of 2,3-dimethylbenzamide, 32.5 g (0.16 mole) of phosphorus pentachloride and 250 ml of AR carbon tetrachloride. The resulting solution was cooled to 30° and 7.4 g (0.16 mole) of 97% formic acid added. Continued to stir at 30° for 20 min. then chilled to 0°, filtered, washed with AR carbon tetrachloride and air-dried to give 36.1 g, m.p. 88°-90°. Heated at 70° for 30 min. a mixture The resulting solution was cooled to 30° then chilled to 0° filtered washed with AR carbon tetrachloride air-dried to give 36.1 g, m.p. 88°-90°

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-pyridin-2-ylpiperazine (16 mg, 0.1 mmol, Aldrich), paraformaldehyde (30 mg, 1 mmol), 2,3-dimethylbenzamide (75 mg, 0.5 mmol, Lancaster), and 42 mg of potassium carbonate (0.3 mmol) in 2 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 29 mg (88%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 2.20 (s, 3H), 2.24 (s, 3H), 2.61 (t, J=4 Hz, 4H), 3.48 (t, J=4 Hz, 4.15 (d, J=5 Hz, 1H), 6.62 (t, J=5 Hz, 1H), 6.81 (d, J=6 Hz, 1H), 7.03 (m, 2H), 7.21 (t, J=5 Hz, 1H), 7.51 (t, J=6 Hz, 1H), 8.12 (d, J=5 Hz, 1H), 8.52 (t, J=5 Hz, 1H); MS (ESI/APCI−) m/e 323 (M−H)+. was heated to reflux under nitrogen overnight filtered the solvent was removed The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate)