| Identification | Back Directory | [Name]
8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolinone | [CAS]
530084-79-8 | [Synonyms]
EOS-62123
8-(Benzylox
-8-(Benzyloxy)
quinolin-2(1H)
-5-(2-bromo-1-hydroxyethyl)
(R)-8-Benzyloxy-5-(2-broMo-1-hydroxyethyl)carbostyril
8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolinone
8-Benzyloxy-5((R)-2-broMo-1-hydroxyethyl)-2-(1H)-quinoline
8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolin-2-one
5-(2-BroMo-(R)-1-hydroxyethyl)-8-benzyloxy-2(1H)-quinolinone
8-benzyloxy-5((R)-2-broMo-1-hydroxyethyl)-2-(1H-)-quinolinone
(R)-8-(Benzyloxy)-5-(2-broMo-1-hydroxyethyl)quinolin-2(1H)-one
8-(Benzyloxy)-5-((1R)-2-bromo-1-hydroxyethyl)quinolin-2(1H)-one
5-[(1R)-2-BroMo-1-hydroxyethyl]-8-(phenylMethoxy)-2(1H)-quinolinone
2(1H)-Quinolinone, 5-[(1R)-2-bromo-1-hydroxyethyl]-8-(phenylmethoxy)-
8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]-1,2-dihydroquinolin-2-one | [Molecular Formula]
C18H16BrNO3 | [MDL Number]
MFCD20484048 | [MOL File]
530084-79-8.mol | [Molecular Weight]
374.23 |
| Chemical Properties | Back Directory | [Melting point ]
>153oC (dec.) | [Boiling point ]
595.8±50.0 °C(Predicted) | [density ]
1.490±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
10.78±0.70(Predicted) | [color ]
Light Beige | [InChI]
InChI=1S/C18H16BrNO3/c19-10-15(21)13-6-8-16(18-14(13)7-9-17(22)20-18)23-11-12-4-2-1-3-5-12/h1-9,15,21H,10-11H2,(H,20,22)/t15-/m0/s1 | [InChIKey]
GNFMSZCSSUZAGV-HNNXBMFYSA-N | [SMILES]
N1C2=C(C([C@@H](O)CBr)=CC=C2OCC2=CC=CC=C2)C=CC1=O |
| Hazard Information | Back Directory | [Chemical Properties]
Light Brown Solid | [Uses]
8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolinone is used in the preparation of phenylethanolamine derivatives as β2 adrenoreceptor agonists.
| [Synthesis]
General procedure for the synthesis of 8-benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one from 1-(8-(benzyloxy)-2-hydroxyquinolin-5-yl)-2-bromoacetophenone: Under nitrogen protection, the tetrahydrofuran (1400 mL) and 1-(8-(benzyloxy)-2-hydroxyquinolin-5-yl)-2-bromoacetophenone (100 g) were The mixture was cooled to 0-5°C. Subsequently, R-methyl CBS (7.5 g) was slowly added and boron dimethyl sulfide complex (24.3 g) was added at 0-10°C. The reaction was carried out at 0-10°C. The reaction was carried out at 0-10°C. The reaction mixture was stirred at 0-10°C for 1-2 h. The reaction progress was monitored by HPLC. Upon completion of the reaction, methanol (100 mL) was slowly added and stirring was continued at 0-10°C for 15 min. Subsequently, the reaction mixture was distilled under vacuum at 40-45°C and then cooled to 25-30°C. The cooled reaction mixture was slowly added to hydrochloric acid solution and stirred for 1-2 h at 25-30°C. The reaction mixture was then purified by HPLC. The resulting solid was filtered, washed with water (300 mL) and dried at 65-70°C for 8 hours. The product yield was 95%. | [References]
[1] Patent: US2016/326118, 2016, A1. Location in patent: Paragraph 0067; 0068
[2] Patent: US2004/224982, 2004, A1. Location in patent: Page 3; 10
[3] Patent: US2004/242622, 2004, A1. Location in patent: Page 30
[4] Patent: US2004/167167, 2004, A1. Location in patent: Page/Page column 34
[5] Patent: US2006/35933, 2006, A1. Location in patent: Page/Page column 25 |
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