4-Hydroxy-2-methylquinoline

Base Information

• Chemical Name: 4-Hydroxy-2-methylquinoline
• CAS No.: 607-67-0
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• Hs Code.: 29334900
• European Community (EC) Number: 210-140-6
• NSC Number: 21483
• DSSTox Substance ID: DTXSID40209515
• Nikkaji Number: J58.018J,J3.101.292I
• Wikidata: Q72480444
• ChEMBL ID: CHEMBL1256109
• Mol file: 607-67-0.mol

Synonyms:4-Hydroxy-2-methylquinoline;2-Methylquinolin-4-ol;607-67-0;5660-24-2;2-methylquinolin-4(1H)-one;2-Methyl-4-quinolinol;4-Quinolinol, 2-methyl-;2-methyl-1H-quinolin-4-one;2-Methyl-4-hydroxyquinoline;4-Hydroxyquinaldine;2-Methyl-quinolin-4-ol;2-methyl-4(1H)-Quinolinone;2-methyl-quinolin-4(1H)-one;EINECS 210-140-6;MFCD00006758;MFCD00518775;NSC21483;VFH;1H-4-Oxoquinaldine;Maybridge1_000216;Oprea1_457343;Oprea1_710493;MLS000084685;SCHEMBL266459;2-Methylquinoline-4(1H)-one;CHEMBL1256109;HMS542B18;NWINIEGDLHHNLH-UHFFFAOYSA-;DTXSID40209515;CHEBI:194391;HMS2364A23;KUC100216N;AMY23277;c1269;CCG-44041;NSC 21483;NSC-21483;STK024344;STK054930;ZB0110;2-methyl-1,4-dihydroquinolin-4-one;AKOS000265038;AKOS003238098;4-Hydroxy-2-methylquinoline, 98.5%;SB67513;SB67949;SMR000019032;SY048580;TS-02117;A8457;CS-0019244;CS-0159505;FT-0618748;FT-0694543;M2620;C21873;D82318;EN300-129304;F16203;AB00404214-09;AH-034/32851007;J-650319;Q-102032;SR-01000620630-2;F0451-0420;Z445211720

Chemical Property of 4-Hydroxy-2-methylquinoline

Chemical Property:

• Appearance/Colour: BEIGE POWDER
• Vapor Pressure: 0.00669mmHg at 25°C
• Melting Point: 234-236 °C(lit.)
• Refractive Index: 1.573
• Boiling Point: 270.8 °C at 760 mmHg
• PKA: 4.44±0.40(Predicted)
• Flash Point: 120.1 °C
• PSA: 33.12000
• Density: 1.136g/cm3
• LogP: 2.24880
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 232

Purity/Quality:

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

2-Methylquinolin-4-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=O)C2=CC=CC=C2N1
• Uses: 4-Hydroxy-2-methylquinoline is act as an intermediate in the synthesis of dequalinium chloride and as pharmaceutical intermediate. 4-Hydroxy-2-methylquinoline can be used as an intermediate in the synthesis of a wide range of medicinally important compounds such as:Synthesis of 2-(quinolin-4-yloxy)acetamides as potent antitubercular agents.Synthesis of 2-arylethenylquinoline derivatives for the treatment of Alzheimer′s disease.Synthesis of 1,10-diethoxy-1H-pyrano[4,3-b]quinolones as antibacterial agents.Synthesis of phenylimidazole-pyrazolo[1,5-c]quinazolines as potent phophodiesterase 10A (PDE10A) inhibitors.

Technology Process of 4-Hydroxy-2-methylquinoline

There total 24 articles about 4-Hydroxy-2-methylquinoline 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%

4-chloro-2-methylquinoline (4295-06-1) → 4-hydroxy-2-methylquinoline (607-67-0)

Guidance literature:

4-chloro-2-methylquinoline; With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole; In 1,4-dioxane; water; at 100 ℃; for 20h; Inert atmosphere;

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.200804898

Reference yield: 99.0%

2-methylquinolin-4-yl acetate (117498-01-8) → 4-hydroxy-2-methylquinoline (607-67-0) + C10H9N(18)O

Guidance literature:

With acetic acid; ¹⁸O-labeled water; sodium chloride; at 50 ℃; for 24h; Product distribution;

DOI:10.1021/jo00262a037

Reference yield: 92.0%

acetoacetic acid-ethylester-anil (587-95-1) → 4-hydroxy-2-methylquinoline (607-67-0)

Guidance literature:

In tetrahydrofuran; at 360 - 370 ℃; for 0.0125h; under 97509.8 Torr; regioselective reaction; Flash vacuum pyrolysis; Autoclave;

DOI:10.1016/j.tetlet.2011.11.125

upstream raw materials:

3-phenylaminobut-2-enoic acid ethyl ester

2-methylquinoline-4-carboxylic acid

2-methyl-2,3-dihydroquinolin-4(1H)-one

methyl 3-phenylaminobut-2-enoate

Downstream raw materials:

2-[2-(2-chlorophenyl)vinyl]quinolin-4-ol

sulfotep

Quinothion

4-methoxy-2-methyl-quinoline

Refernces

• 1、 Muscio, Oliver J.,Theobald, Paula G.,Rutherford, Denise R.. "Hydrolyses of 2- and 4-Fluoro N-Heterocycles. 3. Nucleophilic Catalysis by Buffer Bases in the General Acid Catalyzed Hydrolysis of 4-Fluoroquinaldine". . p. 166 - 171. Retrieved 1989.
• 2、 Huang, Guang,Murillo Solano, Claribel,Melendez, Joel,Shaw, Justin,Collins, Jennifer,Banks, Robert,Arshadi, Arash Keshavarzi,Boonhok, Rachasak,Min, Hui,Miao, Jun,Chakrabarti, Debopam,Yuan, Yu. "Synthesis, Structure-Activity Relationship, and Antimalarial Efficacy of 6-Chloro-2-arylvinylquinolines". . p. 11756 - 11785. Retrieved 2020/11/26.
• 3、 Mo, Jun,Yang, Hongyu,Chen, Tingkai,Li, Qihang,Lin, Hongzhi,Feng, Feng,Liu, Wenyuan,Qu, Wei,Guo, Qinglong,Chi, Heng,Chen, Yao,Sun, Haopeng. "Design, synthesis, biological evaluation, and molecular modeling studies of quinoline-ferulic acid hybrids as cholinesterase inhibitors". . . Retrieved 2019/10/05.