Hydrochloric Acid → HCID 86669828, compound

Participants

Reaction Steps

To a solution of 3-[1,3]dioxolan-2-yl-2-ethyl-6-methoxyquinoline SMA 44002 (400 mg, 1.54 mmol) in THF (10 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added a 1 N aqueous HCl solution (5 mL) and the mixture was stirred overnight at RT, then for 1 h at 70° C. A 6 N aqueous HCl solution (2.5 mL) was then added and the mixture was stirred for 26 h at 70° C. THF was removed at 40° C. under vacuum before addition of a conc. NH4OH solution (5 mL). The solution was extracted with CH2Cl2 (50 mL) and the organic phase was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum to give 2-ethyl-6-methoxyquinoline-3-carbaldehyde SMA 44004 as a brown oil (269 mg, 81% yield).

Provenance & Evidence