Hydrochloric Acid → HCID 90082926, compound

To a solution of 1,2,3,4-tetrahydroquinoxaline (50 g, 373 mmol) in toluene (Ratio: 20 times, Volume: 20 mL) at 0° C. was added BCl3 (1M solution in DCM, 9.0 mL, 447 mmol). Then aluminum chloride (59.6 g, 447 mmol) and 3-chlorobenzonitrile (61.5 g, 447 mmol) were added. The reaction mixture was warmed up to room temperature and heated at 110° C. for 8 h. The reaction mixture was cooled to room temperature. HCl (15.0 mL, 1.5 N) was added and the mixture was heated at 110° C. for 3 h. The reaction mixture was cooled to room temperature and basified with 10% NaHCO3. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated to give a crude material. This crude material was purified via BIOTAGE®, eluted with 20% EtOAC/hexane to afford (3-chlorophenyl)(1,2,3,4-tetrahydroquinoxalin-5-yl)methanone, Intermediate E-1C (50 g, 183 mmol, 49.2% yield)1H NMR (400 MHz, CDCl3) δ ppm 8.6 (1H, bs), 7.6 (1H, s), 7.5 (2H, m), 7.4 (1H, m), 6.8 (1H, m), 6.6 (1H, m), 6.4 (1H, m), 3.8 (1H, bs), 3.6 (2H, m), 3.4 (2H, m).

1. temperatureheated at 110° C. for 8 h
2. temperatureThe reaction mixture was cooled to room temperature
3. temperaturethe mixture was heated at 110° C. for 3 h
4. extractionThe aqueous layer was extracted with EtOAc
5. washThe combined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto give a crude material
10. customThis crude material was purified via BIOTAGE®
11. washeluted with 20% EtOAC/hexane

ORD record

ord-56af083749ff47a3b018e780d1df80ec

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249157B2