1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone

Base Information

• Chemical Name: 1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone
• CAS No.: 27392-71-8
• Molecular Formula: C11H14N2O
• Molecular Weight: 190.24200
• DSSTox Substance ID: DTXSID80434864
• Nikkaji Number: J3.198.314B
• Wikidata: Q82249424

Synonyms:27392-71-8;1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone;1-(6-amino-3,4-dihydro-2H-quinolin-1-yl)ethanone;1-(6-amino-1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one;6-Quinolinamine, 1-acetyl-1,2,3,4-tetrahydro-;SCHEMBL7416330;DTXSID80434864;CBA39271;AKOS000225126;1-Acetyl-6-amino-1,2,3,4-tetrahydroquinoline;EN300-145559;F2189-0475

Chemical Property of 1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone

Chemical Property:

• Boiling Point: 477.5±45.0 °C(Predicted)
• PKA: 3.78±0.20(Predicted)
• PSA: 46.33000
• Density: 1.182±0.06 g/cm3(Predicted)
• LogP: 2.21410
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 190.110613074
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

97% ^*data from raw suppliers

1-(6-Amino-3,4-dihydroquinolin-1(2H)-yl)ethanone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1CCCC2=C1C=CC(=C2)N

Technology Process of 1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone

There total 9 articles about 1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone 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: 79.0%

1-(1,2,3,4-tetrahydro-6-nitroquinolinyl)ethanone (14026-46-1) → 1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone (27392-71-8)

Guidance literature:

With tin(ll) chloride; In ethanol; at 70 ℃; for 22h;

DOI:10.1021/jo400398y

Reference yield:

N-(1-acetyl-1,2,3,4-tetrahydro-6-quinolyl)trifluoroacetamide (158942-58-6) → 1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone (27392-71-8)

Guidance literature:

With sodium hydroxide; In ethanol; 1.) RT, 30 min, 2.) reflux, 30 min;

DOI:10.1021/jm00014a004

Reference yield:

6-aminoquinoline (580-15-4) → 1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone (27392-71-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / Et₃N / CHCl₃ / 1 h

2: 73 percent / NiCl₂*6H₂O, NaBH₄ / methanol / 1 h

3: 79 percent / pyridine / CH₂Cl₂ / 0.5 h

4: aq. NaOH / ethanol / 1.) RT, 30 min, 2.) reflux, 30 min

With pyridine; sodium hydroxide; sodium tetrahydroborate; triethylamine; nickel dichloride; In methanol; ethanol; dichloromethane; chloroform;

DOI:10.1021/jm00014a004

upstream raw materials:

N-(1-acetyl-1,2,3,4-tetrahydro-6-quinolyl)trifluoroacetamide

6-aminoquinoline

N-(6-quinolyl)trifluoroacetamide

N-(1,2,3,4-tetrahydro-6-quinolyl)trifluoroacetamide

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