8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolinone Chemical Properties

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

8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolinone Usage And Synthesis

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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