7-Bromoquinolin-2(1H)-one
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7-Bromoquinolin-2(1H)-one
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CAS No:
99465-10-8
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Formula:
C9H6BrNO
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Chemical Name:
7-Bromoquinolin-2(1H)-one
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Synonyms:
2(1H)-Quinolinone,7-bromo-;7-Bromo-2(1H)-quinolinone;7-Bromoquinolin-2(1H)-one;7-Bromo-2-hydroxyquinoline;7-Bromoquinoline-2(1H)-one;7-Bromo-2-quinolinone;7-Bromo-1,2-dihydroquinolin-2-one
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CAS No:
7-Bromoquinolin-2(1H)-one Use and Manufacturing
A stirred solution mixture of 7-bromo-2-chloroquinoline (5.0 g, 20.6 mmol) in 5 M aqueous hydrochloric acid (133 mL) and 1, 4-dioxane (14 mL) was heated at reflux for 2 h. The reaction was cooled and the resulting precipitate was collected by filtration and washed with water to afford the subtitled compound as a colourless solid (4.3 g, 93percent). A stirred solution mixture of 7-bromo-2-chloroquinoline (5.0 g, 20.6 mmol) in 5 M aqueous hydrochloric acid (133 mL) and 1, 4-dioxane (14 mL) was heated at reflux for 2 h. 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%.Example 6:- re/-1 -f3-r(3aR*, 7aS*)-2-oxo-1 -f3-oxo-2H, 3H, 4H-pyridor3, 2-bin, 41oxazin-6- yl)-octahvdro-ri , 31oxazolor5, 4-clpyridin-5-vnpropyl)-2-oxo-1 , 2-dihvdroquinoline-7- carbonitrile a) 7-bromo-1-(3, 3-dimethoxypropyl)-1 , 2-dihydroquinolin-2-one 6a A solution of 7-bromo-1 , 2-dihydroquinolin-2-one (1.5 g, 6.68 mmol), 3-bromo-1 , 1- dimethoxypropane (0.96 ml_, 7.03 mmol) and cesium carbonate (6.54 g, 20.03 mmol) in DMF (100 ml_) was heated for 17 h at 100 C. After cooling, H20 (250 ml_) was added and the mixture extracted with EtOAc (3 x 100 ml_). The combined extracts were dried (MgS04), filtered and concentrated under reduced pressure. The residue was purified via silica gel chromatography using 0-100% EtOAc in pet. ether to give 7-bromo-1-(3, 3- dimethoxypropyl)-1 , 2-dihydroquinolin-2-one 6a (740 mg, 34%) as a colourless solid. LC-MS (Method A) 296.0 [M-OMe]+; RT 2.78 min.A solution of 7-bromo-1 , 2-dihydroquinolin-2-one (1.5 g, 6.68 mmol), 3-bromo-1 , 1- dimethoxypropane (0.96 mL, 7.03 mmol) and cesium carbonate (6.54 g, 20.03 mmol) in DMF (100 mL) were heated for 17 h at 100 C. After cooling, H20 (250 mL) was added and the mixture extracted with EtOAc (3 x 100 mL). The combined extracts were dried (MgSCU), filtered and concentrated under reduced pressure. The residue was purified via silica gel chromatography using 0-100% EtOAc in pet. ether to give 7-bromo-1-(3, 3- dimethoxypropyl)-1 , 2-dihydroquinolin-2-one 14a (740 mg, 34%) as a colourless solid. LC- MS (Method A) 296.0 [M-OMe]+, RT 2.78 min.A solution of 7-bromo-1 , 2-dihydroquinolin-2-one (1.5 g, 6.68 mmol), 3-bromo-1 , 1- dimethoxypropane (0.96 ml_, 7.03 mmol) and cesium carbonate (6.54 g, 20.03 mmol) in DMF (100 ml_) washeated overnight at 100C. H20 (250 ml_) was added, extracted with EtOAc (3 x 100 ml_), dried with MgS04 and concentrated under reduced pressure. The residue was purified via silica gel chromatography eluting with (0-100% EtOAc in petroleum ether) to give a colourless solid as 7-bromo-1-(3, 3-dimethoxypropyl)-1 , 2-dihydroquinolin-2- one 60a (740 mg, 34%). LC-MS (Method A) 296.0 [M-OMe]+; RT 2.78 min.
Computed Properties
Molecular Weight:224.05
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:222.96328
Monoisotopic Mass:222.96328
Topological Polar Surface Area:29.1
Heavy Atom Count:12
Complexity:227
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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