Hydrochloric Acid → HCID 60048684, compound

To a solution of 2-cyano-4-methoxypyridine 153 (503 mg, 3.75 mmol) in benzene: ether (20 mL, 1:1, v/v) cooled at 0° C. was added dropwise 1 M solution of EtMgBr (5 mL, 5 mmol) in THF and the mixture was allowed to warm to room temperature with stirring. After 4 hr, the reaction flask was cooled again at 0° C. and 2.3 mL of hydrochloric acid (10%) was added dropwise, with additional five minutes stirring. Then, the mixture was poured in dichloromethane (80 mL) and water (60 mL) and the pH of the aqueous layer was adjusted to 10 with a 10% aqueous solution of sodium hydroxide. The resulted mixture was extracted with dichloromethane (3×80 mL). The combined organic layer was dried by filtration over anhydrous MgSO4 and the filtrate was concentrated to provide 694 mg of the crude ketone 154. The product was used without purification for the step; 1H NMR (acetone d6)δ: 1.14 (t, 3H, J=7.3 Hz), 3.20 (q, 2H, J=7.3 Hz), 3.97 (s, 3H), 7.16 (dd, 1H, J=5.6 & 2.6 Hz), 7.50 (d, 1H, J=2.6 Hz), 8.52 (d, 1H, =5.6 Hz).

1. temperaturethe reaction flask was cooled again at 0° C.
2. stirringstirring
3. extractionThe resulted mixture was extracted with dichloromethane (3×80 mL)
4. dry with materialThe combined organic layer was dried by filtration over anhydrous MgSO4
5. concentrationthe filtrate was concentrated

ORD record

ord-f7211042e88f41dd8c7c1e12251069ee

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090651B2