7-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONE

Peachy Solid

To a 500 mL two-neck round-bottom flask fitted with a magneticstir bar and argon inlet was charged 7-[4-bromobutoxy]-3, 4-dihydro-2(1H)-quinolinone 5b (10 g, 0.033 mol) in THF(200 mL). To the aforementioned mixture 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (30.4 g, 0.13 mol) was added and the contents were stirred at rt until the completion of the reaction.Upon the consumption of starting material (as indicatedby TLC), THF was evaporated under reduced pressure. Theresidual product obtained was washed with water (200 mL)and extracted with ethyl acetate (3 × 100 mL). The organiclayer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to furnish the crudeproduct. The crude product was purified by column chromatographyusing Ethyl acetate and n-Hexane as solventsystem to afford the title compound 8b.Yield: 98.99percent (9.8 g);1H NMR (400 MHz, DMSO-d6) δ 11.57 (s, 1H), 7.77 (d, J = 9.4 Hz, 1H), 7.53 (d, J = 9.4 Hz, 1H), 6.83–6.69 (m, 2H), 6.27 (d, J = 9.6 Hz, 1H), 4.02 (t, J = 6.1 Hz, 2H), 3.59(t, J = 6.6 Hz, 2H), 2.03–1.89 (m, 2H), 1.89–1.74 (m, 2H);13C NMR (100 MHz, DMSO-d6): δ 162.67, 160.72, 141.05, 140.44, 129.69, 118.97, 113.77, 111.19, 99.05, 67.28, 35.26, 29.46, 27.74; ESI (MS): 296 [M+H]+; HPLC purity: 99.26percent[RT: 11.545 min; UV detection at 210 nm; Column: X BridgeC-18, 150 × 4.6 mm, 5 μm particle size; Mobile phase: A)0.1percent TFA in water, B) Acetonitrile; T/percentB: 0/10, 3/10, 15/95, 23/95, 25/10, 30/10; Flowrate: 1.0 mL/min;Diluent:Acetonitrile:Water (80:20)]. 1H NMR spectral data of 8b was foundto be consistent with the values reported in Ref. 16.Intermediate 14:[0130] AICICompound 2c (30g, 100.67mmol), DDQ (25.1g, 110 . 57mmol) into 1L reaction bottle, by adding 1, 4-dioxane 300 ml, stirring under 95 °C 2 hours, TLC monitoring reaction is ended, concentrated under reduced pressure, by adding ice water, then adding sodium thiosulfate aqueous solution, stirring, add 3L dichloromethane extraction, separating the organic layer, an organic layer saturated salt water for washing, drying of anhydrous sodium sulfate, filtered, concentrated to obtain 29.6g strawcoloured solid 1c, almost quantitative yield, directly without further purification in the next step.

Molecular Weight:296.16
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:295.02079
Monoisotopic Mass:295.02079
Topological Polar Surface Area:38.3
Heavy Atom Count:17
Complexity:293
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes