HCID 21877762, compound → 8-Fluoro-6-nitro-1,2,3,4-tetrahydroquinoline

Temperature

0 °C

To a stirred solution of 8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (950 mg, 4.52 mmol) in tetrahydrofuran (5 ml) was added borane-tetrahydrofuran complex (45.2 ml, 45.2 mmol) as a solution in THF. The reaction mixture was then heated to reflux temperature overnight. The reaction mixture was then cooled to 0° C. and quenched with methanol. The quenched mixture was then concentrated in vacuo, redissolved in methanol and reconcentrated, then refluxed in methanol for 2 h. The mixture was then concentrated onto silica gel, and chromatographed using 0-20% ethyl acetate in hexanes. 1H NMR (DMSO-d6) δ 7.77-7.71 (m, 1H), 7.73 (m, 1H), 7.31 (brs, 1H), 3.35-3.28 (m, 2H), 2.77 (t, J=6.2 Hz, 2H), 1.85-1.77 (m, 2H).

1. temperatureThe reaction mixture was then heated
2. temperatureto reflux temperature overnight
3. customquenched with methanol
4. concentrationThe quenched mixture was then concentrated in vacuo
5. dissolutionredissolved in methanol
6. temperaturerefluxed in methanol for 2 h
7. concentrationThe mixture was then concentrated onto silica gel
8. customchromatographed

ORD record

ord-e0691f3898e14f7685bbbe9f125a64ad

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173813B2