Dimethyl Sulfoxide → HCID 58118602, compound

A 1-L flask was charged with methyl 5,6,7,8-tetrahydroquinoline-6-carboxylate (12.53 g, 65.52 mmol), chloroform (400 mL) and m-chloroperbenzoic acid (22.6 g, 91.7 mmol). The resulting solution was stirred at room temperature for 1 hour then dimethyl sulfoxide (2.8 mL, 39 mmol) was added to quench any remaining m-chloroperbenzoic acid and stirred at room temperature for 30 minutes. The mixture was poured into 2M Na2CO3 (400 mL). The aqueous layer was extracted with CHCl3 (3×200 mL), dried (Na2SO4), filtered and concentrated to afford a white solid (16.67 g). Chromatography on silica (0-15% MeOH in DCM) produced an off white solid (13.90 g, greater than theoretical), which was carried forward without additional purification. m/z=208.3 (M+H)+. NMR (400 MHz, CDCl3) δ 8.16 (d with fine str., J=5.8 Hz, 1H), 7.10-7.03 (m, 2H), 3.74 (s, 3H), 3.20 (app dt, J=13.9, 5.6 Hz, 1H), 3.11-2.99 (m, 2H), 2.93-2.82 (m, 1H), 2.79-2.71 (m, 1H), 2.39-2.30 (m, 1H), 2.05-1.92 (m, 1H).

1. customto quench any remaining m-chloroperbenzoic acid
2. stirringstirred at room temperature for 30 minutes
3. additionThe mixture was poured into 2M Na2CO3 (400 mL)
4. extractionThe aqueous layer was extracted with CHCl3 (3×200 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-e6b78fd548f54fc7b0a5ee984502a909

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153651B2