Hydrochloric Acid → HCID 86669832, compound

Participants

Reaction Steps

To a solution of 2-butyl-3-(1,3-dioxolan-2-yl)-6-methoxyquinoline SMA 44042 (847 mg, 2.95 mmol) in THF (20 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added a 12 N aqueous HCl solution (5.0 mL, 60.0 mmol) and the mixture was stirred overnight at RT then for 3 h at 70° C. After cooling to RT, THF was removed at 40° C. under vacuum before addition of a 10 N aqueous NaOH solution until neutral pH. The residue was then taken up in CH2Cl2 (50 mL) and the organic layer was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent CH2Cl2:EtOAc=100:0 to 98:2) gave 2-butyl-6-methoxyquinoline-3-carbaldehyde SMA 44044 as an orange solid (583 mg, 81% yield).

Provenance & Evidence