7-Bromo-3,4-dihydro-1H-quinolin-2-one

The compound 6-bromo-2, 3-dihydro-1H-inden-1-one (2.0 g, 9.5 mmol) was dissolved in chloroform (30 mL)Methanesulfonic acid (6 mL) was then added dropwise to the reaction system, Finally, sodium azide (1.90 g, 9.5 mmol) was added portionwise to the reaction system, Reflux for three hours.After completion of the reaction, the mixture was cooled to room temperature, and then the reaction solution was poured into ice water. The mixture was separated and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried over anhydrous sodium sulfate, filtered and dried. The crude product was purified by column chromatography (Petroleum ether / ethyl acetate: 2/1) to give 7-bromo-3, 4-dihydroquinolin-2 (1H) -one(0.90 g) in 42percent yield.Compound I-8 (226 mg, 1 mmol), ferric trichloride hexahydrate (2.7 mg, 0.01 mmol) and sodium peroxodisulfate (286 mg, 1.2 mmol) were added to a reaction flask with a reflux condenser and acetonitrile (5 mL) was added. ) And water (5 mL) and stir well at room temperature. The mixture was stirred with heating at 80 C for 5-6 hours until the reaction was complete. The reaction mixture was concentrated by heating to remove most of the acetonitrile, and then slowly cooled to room temperature, and a solid was slowly precipitated. The product II-8 was isolated by filtration and drying to obtain 94 mg of an off-white solid with a yield of 42%.Potassium nitrate (134 mg, 1.33 mmol) was added portion-wise to a mixture of 7-bromo-3, 4- dihydro-1H-quinolin-2-one (250 mg, 1.11 mmol) in sulfuric acid (7 mL). The mixture was stirred at 0 C to ambient temperature for 1 h. The reaction mixture was poured onto ice and extracted with isopropyl acetate. The solids that would not dissolve were first filtered off anddried under hi-vacuum. The organic extracts were washed with water, saturated sodium bicarbonate solution, and brine. The combined organics were dried over sodium sulfate and concentrated under reduce pressure to afford 7-bromo-6-nitro-3 , 4-dihydroquinolin-2( 1 H)-one (300 mg, quant.) as a yellow solid, which was carried on without further purification. 'H NMR (400 MHz, DMSO-d6) oe 10.60 (s, 1H), 8.02 (s, 1H), 7.23 (s, 1H), 2.96 (t, J =7.7 Hz, 2H), 2.57-2.51 (m, 2H).

Molecular Weight:226.07
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:224.97893
Monoisotopic Mass:224.97893
Topological Polar Surface Area:29.1
Heavy Atom Count:12
Complexity:195
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes