5-Chloro-2,3-dihydroquinolin-4(1H)-one

Base Information

• Chemical Name: 5-Chloro-2,3-dihydroquinolin-4(1H)-one
• CAS No.: 21617-16-3
• Molecular Formula: C9H8ClNO
• Molecular Weight: 181.622
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID20505542
• Wikidata: Q82360743
• Mol file: 21617-16-3.mol

Synonyms:21617-16-3;5-CHLORO-2,3-DIHYDROQUINOLIN-4(1H)-ONE;5-CHLORO-1,2,3,4-TETRAHYDROQUINOLIN-4-ONE;5-CHLORO-2,3-DIHYDRO-1H-QUINOLIN-4-ONE;4(1H)-Quinolinone, 5-chloro-2,3-dihydro-;5-CHLORO-2,3-DIHYDRO-4(1H)-QUINOLINONE;SCHEMBL9803698;DTXSID20505542;WAA61716;MFCD10697716;AKOS006303412;AB60319;BS-15917;5-chloro-2, 3-dihydro-1H-quinolin-4-one;CS-0197013;EN300-175531;Y10805

Chemical Property of 5-Chloro-2,3-dihydroquinolin-4(1H)-one

Chemical Property:

• PSA: 29.10000
• LogP: 2.47630
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 181.0294416
• Heavy Atom Count: 12
• Complexity: 195

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CNC2=C(C1=O)C(=CC=C2)Cl

Technology Process of 5-Chloro-2,3-dihydroquinolin-4(1H)-one

There total 3 articles about 5-Chloro-2,3-dihydroquinolin-4(1H)-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: 51.0%

1-(3-chlorophenyl)-azetidin-2-one (76227-98-0) → 7-chloro-1,2,3,4-tetrahydroquinolin-4-one (21617-15-2) + 5-chloro-2,3-dihydro-4(1H)-quinolinone (21617-16-3)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 0 - 18 ℃; for 1h; Inert atmosphere;

DOI:10.1071/CH10465

Reference yield:

N-(3-chlorophenyl)-N-<(4-methylphenyl)sulfonyl>-β-alanine (66737-56-2) → 7-chloro-1,2,3,4-tetrahydroquinolin-4-one (21617-15-2) + 5-chloro-2,3-dihydro-4(1H)-quinolinone (21617-16-3)

Guidance literature:

With PPA; at 110 ℃; for 0.75h;

DOI:10.1016/0223-5234(93)90036-E

Reference yield:

3-iodochlorobenzene (625-99-0) → 7-chloro-1,2,3,4-tetrahydroquinolin-4-one (21617-15-2) + 5-chloro-2,3-dihydro-4(1H)-quinolinone (21617-16-3)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(l) iodide; potassium carbonate / toluene / 20 h / 18 - 140 °C / Inert atmosphere; Sealed

2: trifluorormethanesulfonic acid / dichloromethane / 1 h / 0 - 18 °C / Inert atmosphere

With copper(l) iodide; trifluorormethanesulfonic acid; potassium carbonate; In dichloromethane; toluene; 1: Goldberg-Buchwald cross-coupling / 2: Fries rearrangement;

DOI:10.1071/CH10465

upstream raw materials:

N-(3-chlorophenyl)-N-<(4-methylphenyl)sulfonyl>-β-alanine

1-(3-chlorophenyl)-azetidin-2-one

3-iodochlorobenzene