2-Methyl-6-nitroquinolin-4-ol

Base Information

• Chemical Name: 2-Methyl-6-nitroquinolin-4-ol
• CAS No.: 112219-43-9
• Molecular Formula: C10H8N2O3
• Molecular Weight: 204.185
• European Community (EC) Number: 653-604-7
• NSC Number: 30292
• DSSTox Substance ID: DTXSID90283188
• Nikkaji Number: J1.427.629G
• Wikidata: Q82017669
• Mol file: 112219-43-9.mol

Synonyms:1207-82-5;2-methyl-6-nitroquinolin-4-ol;2-METHYL-6-NITROQUINOLIN-4(1H)-ONE;2-methyl-6-nitro-1H-quinolin-4-one;4-Hydroxy-2-methyl-6-nitroquinoline;112219-43-9;2-Methyl-6-nitro-4-quinolinol;NSC30292;Oprea1_617288;SCHEMBL2993366;DTXSID90283188;WTJKUGPNJDSKBL-UHFFFAOYSA-N;NSC-30292;STL227701;2-methyl-6-nitro-4(1h)-quinolinone;AKOS000267974;SB71383;EU-0054024;FT-0691790;SR-01000544329;SR-01000544329-1

Chemical Property of 2-Methyl-6-nitroquinolin-4-ol

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 204.05349212
• Heavy Atom Count: 15
• Complexity: 332

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(N1)C=CC(=C2)[N+](=O)[O-]

Technology Process of 2-Methyl-6-nitroquinolin-4-ol

There total 1 articles about 2-Methyl-6-nitroquinolin-4-ol 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: 66.0%

ethyl 3-ethoxy-2-butenoate (998-91-4) + 4-nitro-aniline (100-01-6,104810-17-5) → 2-methyl-6-nitro-1H-quinolin-4-one (112219-43-9)

Guidance literature:

With sulfuric acid; In tetralin; at 150 - 210 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmc.2013.11.009

Reference yield:

2-methyl-6-nitro-1H-quinolin-4-one (112219-43-9) → N-(4-amino-2-methylquinolin-6-yl)-2-phenylacetamide (7511-77-5)

Guidance literature:

Multi-step reaction with 7 steps

1: trichlorophosphate / water / 0.5 h / Reflux; Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere

3: triphenylphosphine / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere

4: pyridine / 1 h / 60 °C / Inert atmosphere

5: ammonium formate; 5%-palladium/activated carbon / methanol / 20 h / 20 °C / Inert atmosphere

6: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

7: dichloromethane

With pyridine; sodium azide; 5%-palladium/activated carbon; ammonium formate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 3: |Staudinger Azide Reduction;

DOI:10.1016/j.bmc.2013.11.009

Reference yield:

2-methyl-6-nitro-1H-quinolin-4-one (112219-43-9) → 1-(4-(bis(2-chloroethyl)amino)phenyl)-3-(4-methylamino-2-methylquinolin-6-yl)urea (1621143-00-7)

Guidance literature:

Multi-step reaction with 4 steps

1: trichlorophosphate / 1 h / Reflux

2: phenol / 5 h / 170 °C

3: acetic acid; iron / ethanol; water / 2 h / Reflux

4: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C

With iron; acetic acid; triethylamine; trichlorophosphate; In ethanol; water; N,N-dimethyl-formamide; phenol;

DOI:10.1016/j.ejmech.2014.06.066

upstream raw materials:

ethyl 3-ethoxy-2-butenoate

4-nitro-aniline

Downstream raw materials:

4-chloro-2-methyl-6-nitroquinoline

4-amino-2-methyl-6-nitroquinoline

N-(4-amino-2-methylquinolin-6-yl)-2-phenylacetamide

1-(4-(bis(2-chloroethyl)amino)phenyl)-3-(4-methylamino-2-methylquinolin-6-yl)urea