2(1H)-Quinolinone, 5-(2R)-oxiranyl-8-(phenylmethoxy)-

Base Information

• Chemical Name: 2(1H)-Quinolinone, 5-(2R)-oxiranyl-8-(phenylmethoxy)-
• CAS No.: 173140-90-4
• Molecular Formula: C18H15NO3
• Molecular Weight: 293.322
• Hs Code.: 2933790090
• Mol file: 173140-90-4.mol

Synonyms:5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone;

Chemical Property of 2(1H)-Quinolinone, 5-(2R)-oxiranyl-8-(phenylmethoxy)-

Chemical Property:

• Boiling Point: 556.0±50.0 °C(Predicted)
• PKA: 10.92±0.70(Predicted)
• PSA: 54.62000
• Density: 1.298
• LogP: 3.17840
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.9% ^*data from raw suppliers

(R)-8-(Benzyloxy)-5-(oxiran-2-yl)quinolin-2(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone is used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Technology Process of 2(1H)-Quinolinone, 5-(2R)-oxiranyl-8-(phenylmethoxy)-

There total 10 articles about 2(1H)-Quinolinone, 5-(2R)-oxiranyl-8-(phenylmethoxy)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one (100331-89-3) → (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone (173140-90-4)

Guidance literature:

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at 0 - 2 ℃; for 1.75h;

With piperidine; water; In tetrahydrofuran; toluene; at 0 - 2 ℃; for 1h; Product distribution / selectivity;

Reference yield:

8-(phenylmethoxy)-5-((R)-2-chloro-1-hydroxy-ethyl)-(1H)-quinolin-2-one → (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone (173140-90-4)

Guidance literature:

With potassium carbonate; In water; acetone; for 5 - 10h; Heating / reflux;

Reference yield:

8-quinolinol (148-24-3,24804-14-6) → (R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone (173140-90-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1,2-dichloro-ethane / 2.25 - 2.33 h / 30 °C

1.2: 15.25 - 16.33 h / 25 - 70 °C

1.3: 0.25 - 0.33 h / 0 - 30 °C

2.1: hydrogenchloride; water / 0.25 - 0.33 h

3.1: potassium carbonate / acetone / 14 h / Heating / reflux

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C

5.1: acetic anhydride / 2 h / 25 - 40 °C

6.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux

6.2: 4.5 h / Heating / reflux

6.3: 30 °C / pH 8 - 9

7.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C

7.2: 1 h / 0 - 2 °C

With hydrogenchloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; water; acetic anhydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetone; toluene;

upstream raw materials:

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

8-quinolinol

5-acetyl-8-hydroxyquinoline

Downstream raw materials:

C₄₄H₄₁N₅O₅S

C₄₃H₄₄N₄O₆S

C₃₄H₃₅N₃O₄

C₄₆H₄₃N₃O₄

Refernces

• 1、 -. "ORGANIC COMPOUNDS". Page/Page column 36. . Retrieved 2008/06/13.
• 2、 -. "PROCESS FOR PREPARING 5-'(R)-2-(5,6-DIETHYL-INDIAN-2-YLAMINO)-1-HYDROXY-ETHYL!-8-HYDROXY-(1H)-QUINOLIN-2-ONE SALT, USEFUL AS AN ADRENOCEPTOR AGONIST". Page/Page column 22. . Retrieved 2008/06/13.