1-Acetyl-1,2-dihydroquinoline

Base Information

• Chemical Name: 1-Acetyl-1,2-dihydroquinoline
• CAS No.: 10174-55-7
• Molecular Formula: C11H11 N O
• Molecular Weight: 173.214
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID20144157
• Nikkaji Number: J48.329J
• Wikidata: Q83008256
• Mol file: 10174-55-7.mol

Synonyms:1-Acetyl-1,2-dihydroquinoline;10174-55-7;1-(2H-quinolin-1-yl)ethanone;Quinoline, 1,2-dihydro-1-acetyl-;BRN 1240674;1-(Quinolin-1(2H)-yl)ethanone;Quinoline, 1-acetyl-1,2-dihydro-;N-acetyl-1,2-dihydroquinoline;SCHEMBL1477941;DTXSID20144157;AKOS030598953;LS-141839

Chemical Property of 1-Acetyl-1,2-dihydroquinoline

Chemical Property:

• Vapor Pressure: 7.89E-06mmHg at 25°C
• Boiling Point: 375.2°C at 760 mmHg
• Flash Point: 184.8°C
• PSA: 20.31000
• Density: 1.14g/cm³
• LogP: 2.13130
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 173.084063974
• Heavy Atom Count: 13
• Complexity: 234

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1CC=CC2=CC=CC=C21

Technology Process of 1-Acetyl-1,2-dihydroquinoline

There total 3 articles about 1-Acetyl-1,2-dihydroquinoline 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: 72.0%

quinoline (91-22-5) + acetic anhydride (108-24-7) → 1-[quinolin-1(2H)-yl]ethan-1-one (10174-55-7) + N-ethyl-1,2,3,4-tetrahydroquinoline (16768-69-7)

Guidance literature:

With sodium tetrahydroborate; In acetic acid; at 60 ℃; for 2h; Product distribution; var. anhydride;

Reference yield:

N-(2-formylphenyl)-N-(3-methylbut-2-en-1-yl)acetamide → quinoline (91-22-5) + 1-[quinolin-1(2H)-yl]ethan-1-one (10174-55-7)

Guidance literature:

With 2,3-diazabicyclo[2.2.1]heptane bis-trifluoroacetic acid; In isopropyl alcohol; at 140 ℃; for 12h; Sealed tube;

DOI:10.1021/acs.orglett.0c02116

Reference yield:

N-(2-formylphenyl)acetamide (13493-47-5) → quinoline (91-22-5) + 1-[quinolin-1(2H)-yl]ethan-1-one (10174-55-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 0.5 h / 0 °C

2.1: 2,3-diazabicyclo[2.2.1]heptane bis-trifluoroacetic acid / isopropyl alcohol / 12 h / 140 °C / Sealed tube

With sodium hydride; 2,3-diazabicyclo[2.2.1]heptane bis-trifluoroacetic acid; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/acs.orglett.0c02116

upstream raw materials:

quinoline

acetic anhydride

N-(2-formylphenyl)acetamide

Downstream raw materials:

3-(2-methylphenyl)quinoline

3-(3-methylphenyl)quinoline

3-(p-methylphenyl)-quinoline

3-(4-(tert-butyl)phenyl)quinoline

Refernces

• 1、 Katayama, Hajime,Ohkoshi, Mitsuko,Yasue, Masaiti. "A Convenient Preparation of N-Acyl-1,2-dihydroquinoline". . p. 2226 - 2228. Retrieved 2007/10/02.