7-(4-Iodobutoxy)-3,4-dihydroquinolin-2-one

Base Information

• Chemical Name: 7-(4-Iodobutoxy)-3,4-dihydroquinolin-2-one
• CAS No.: 952308-47-3
• Molecular Formula: C13H16INO2
• Molecular Weight: 345
• Mol file: 952308-47-3.mol

Synonyms:7-(4-Iodobutoxy)-3,4-dihydroquinolin-2-one;3,4-Dihydro-7-(4-iodobutoxy)-2(1H)-quinolinone;Aripiprazole IMpurity-E

Chemical Property of 7-(4-Iodobutoxy)-3,4-dihydroquinolin-2-one

Chemical Property:

• Boiling Point: 469.3±45.0 °C(Predicted)
• PKA: 14.41±0.20(Predicted)
• PSA: 41.82000
• Density: 1.560±0.06 g/cm3(Predicted)
• LogP: 3.25040
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

7-(4-Iodobutoxy)-3,4-dihydroquinolin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An impurity in the synthesis of Aripiprazole (A771000). A degradation product in Aripiprazole tablets. Aripiprazole Iodobutoxyquinoline Impurity

Technology Process of 7-(4-Iodobutoxy)-3,4-dihydroquinolin-2-one

There total 4 articles about 7-(4-Iodobutoxy)-3,4-dihydroquinolin-2-one 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: 99.0%

7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone (129722-34-5) → 7-(4-iodobutoxy)-3,4-dihydroquinolin-2(1H)-one (952308-47-3)

Guidance literature:

With sodium iodide; In acetone; for 18h; Reflux;

DOI:10.1002/anie.202008482

Reference yield:

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone (22246-18-0) → 7-(4-iodobutoxy)-3,4-dihydroquinolin-2(1H)-one (952308-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / water; acetone / 1 h / 20 °C

1.2: 16 h / 20 °C

2.1: potassium iodide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere

With potassium carbonate; potassium iodide; In water; N,N-dimethyl-formamide; acetone;

Reference yield:

N-(3-methoxyphenyl)-3-chloropropionamide (21261-76-7) → 7-(4-iodobutoxy)-3,4-dihydroquinolin-2(1H)-one (952308-47-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: aluminum (III) chloride / N,N-dimethyl acetamide / 140 - 150 °C

2.1: potassium carbonate / water; acetone / 1 h / 20 °C

2.2: 16 h / 20 °C

3.1: potassium iodide / N,N-dimethyl-formamide / 1 h / 100 °C / Inert atmosphere

With aluminum (III) chloride; potassium carbonate; potassium iodide; In N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetone; 1.1: Friedel Crafts alkylation;

upstream raw materials:

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone

N-(3-methoxyphenyl)-3-chloropropionamide

m-Anisidine

7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone

Downstream raw materials:

7-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-7-oxy)butoxy)-3,4-dihydroquinoline-2(1H)-one

Refernces

• 1、 Pai,Samel. "Synthesis of novel 3,4-dihydroquinolin-2(1H)-one guanidines as potential antihypertensive agents". . p. 1655 - 1660. Retrieved 2012/01/06.