Propylamine → 6-Methoxy-2-(propylamino)quinoline-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (1.50 g, 6.77 mmol) in THF (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added propan-1-amine (5.6 mL, 67.7 mmol) and the reaction mixture was stirred for 1.5 h at 160° C. under microwave irradiation. After cooling to RT, the volatiles were removed at 40° C. under vacuum and the resulting yellow oil was taken up in a mixture of THF:1 N aq. HCl=1:1 (50 mL) and stirred for 1 h at RT. The volatiles were then removed at 40° C. under vacuum and the residue was then neutralised with a saturated NaHCO3 aqueous solution before extraction with CH2Cl2 (100 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under vacuum to give 6-methoxy-2-(propylamino)quinoline-3-carbaldehyde SLA 28172 as an orange solid (1.68 g, 99% yield).

Provenance & Evidence