Azobisisobutyronitrile → 7-Chloro-1,2,3,4-tetrahydroquinolin-2-one

Temperature

120 °C

To a solution of 5-chloro-2-iodoaniline (14.0 g, 0.0552 mol) in dimethyl sulphoxide, ethyl acrylate (30.38 mL, 0.276 mol) and n-tributyltinhydride (22.3 mL, 0.0828 mol), AIBN (3.6 g, 0.022 mol) was added at room temperature. The reaction mixture was heated to 120° C. and stirred for 16 h. The reaction mixture was cooled to room temperature; the reaction mixture was diluted with water. The aqueous phase was extracted with ethyl acetate (3×500 mL), the combined organic layer was washed with cold water, saturated aqueous sodium chloride solution and dried over sodium sulphate, the solvent was evaporated under vacuum and the residue was purified with silica gel (60-120 mesh) silica gel column chromatography by 0-20% ethyl acetate in hexane to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 10.13 (s, 1H), 7.17-7.15 (d, J=7.6 Hz, 1H), 6.93-6.91 (d, J=8.0 Hz, 1H), 6.85 (s, 1H), 2.85-2.81 (t, J=7.2 Hz, 2H), 2.44-2.41 (t, J=8 Hz, 2H); MS (M+1): 181.9.

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionThe aqueous phase was extracted with ethyl acetate (3×500 mL)
3. washthe combined organic layer was washed with cold water, saturated aqueous sodium chloride solution
4. dry with materialdried over sodium sulphate
5. customthe solvent was evaporated under vacuum
6. customthe residue was purified with silica gel (60-120 mesh) silica gel column chromatography by 0-20% ethyl acetate in hexane

ORD record

ord-d977a31cdc344375b39d8f7501bb8bee

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073929B2