Sodium Azide → HCID 117780509, Verbindung

To a solution of 158f (650 mg, 3 mmol) in dichloromethane (6 mL) and methanesulfonic acid (3 mL) was added sodium azide (0.293 mg, 4.5 mmol). See FIG. 4. The reaction mixture was stirred at 20° C. for 16 h. The reaction mixture was partitioned between DCM (50 mL) and aqueous sodium hydroxide solution (50 mL, 1.0 M). The aqueous layer was extracted with DCM (20 mL×3). The combined organic layers were washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:petroleum ether=1:2) to give 6-(trifluoromethoxy)-3,4-dihydroisoquinolin-1(2H)-one 158g (340 mg, 49%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.21 (br s, 1H), 7.20 (s, 1H), 7.13 (d, J=8.8 Hz, 1H), 6.89 (d, J=8.8 Hz, 1H), 2.89 (t, J=7.6 Hz, 2H), 2.48-2.31 (m, 2H)

1. customThe reaction mixture was partitioned between DCM (50 mL) and aqueous sodium hydroxide solution (50 mL, 1.0 M)
2. extractionThe aqueous layer was extracted with DCM (20 mL×3)
3. washThe combined organic layers were washed sequentially with water and brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:petroleum ether=1:2)

ORD-Eintrag

ord-0f71e50188f349c692e04772aa1c8a53

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09326985B2