Ethylamine → HCID 86669834, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-6-ethoxy-7-fluoroquinoline-3-carbaldehyde SMA 44100 (110 mg, 0.43 mmol) in ethylamine (2.0 M in THF, 2.20 mL, 4.40 mmol) in a 10 mL microwave vial equipped with a magnetic stirrer was stirred for 3.5 h at 150° 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=50:50 (10 mL) and the mixture was stirred for 30 min at RT. THF was then removed at 40° C. under vacuum and the residue was basified with a 10 N aq. NaOH solution (pH=8) before extraction with CH2Cl2 (40 mL). The separated organic layer was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 90:10) gave 6-ethoxy-2-(ethylamino)-7-fluoroquinoline-3-carbaldehyde SMA 44102 as a yellow solid (63 mg, 56% yield).

Provenance & Evidence