Ethanamine, 2,2,2-trifluoro- → HCID 86669821, compound

Temperature

160 °C

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 2,2,2-trifluoroethanamine (10.06 mL, 102.0 mmol) and the reaction mixture was stirred for 10 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 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-(2,2,2-trifluoroethylamino)quinoline-3-carbaldehyde SLA 41066 as an orange solid (2.22 g, >100% yield).

1. temperatureAfter cooling to RT
2. customthe volatiles were removed at 40° C. under vacuum
3. additionthe resulting yellow oil was taken up in a mixture of THF
4. stirring1 N aq. HCl=1:1 (50 mL) and stirred for 1 h at RT
5. customThe volatiles were then removed at 40° C. under vacuum
6. extractionthe residue was then neutralised with saturated NaHCO3 aqueous solution before extraction with CH2Cl2 (100 mL)
7. washThe organic phase was washed with brine (20 mL)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under vacuum

ORD record

ord-ef1ed74570d44ab8afa07babff134e57

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772316B2