1,2-Dihydro-6-hydroxy-4-methyl-2-oxo-1-(phenylamino)nicotinonitrile

Base Information

• Chemical Name: 1,2-Dihydro-6-hydroxy-4-methyl-2-oxo-1-(phenylamino)nicotinonitrile
• CAS No.: 835-38-1
• Molecular Formula: C14H13NO
• Molecular Weight: 211.263
• European Community (EC) Number: 279-053-9
• NSC Number: 319039
• DSSTox Substance ID: DTXSID301003486,DTXSID401000259
• Nikkaji Number: J319.218K
• Wikidata: Q82998062
• ChEMBL ID: CHEMBL1867781
• Mol file: 835-38-1.mol

Synonyms:79084-83-6;1,2-Dihydro-6-hydroxy-4-methyl-2-oxo-1-(phenylamino)nicotinonitrile;MLS003115960;EINECS 279-053-9;NSC319039;Oprea1_320934;SCHEMBL3159284;CHEMBL1867781;DTXSID301003486;DTXSID401000259;NSC 319039;NSC-319039;SMR001831520;1-Anilino-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridine-3-carbonitrile;1-Anilino-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Chemical Property of 1,2-Dihydro-6-hydroxy-4-methyl-2-oxo-1-(phenylamino)nicotinonitrile

Chemical Property:

• Vapor Pressure: 7.03E-06mmHg at 25°C
• Melting Point: 102-103 °C
• Boiling Point: 376.9±17.0 °C(Predicted)
• PKA: 0.47±0.10(Predicted)
• PSA: 43.09000
• Density: 1.148±0.06 g/cm3(Predicted)
• LogP: 3.27540
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 241.085126602
• Heavy Atom Count: 18
• Complexity: 464

Purity/Quality:

95% ^*data from raw suppliers

1-(2-Aminophenyl)-2-phenylethanone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)N(C(=C1C#N)O)NC2=CC=CC=C2

Technology Process of 1,2-Dihydro-6-hydroxy-4-methyl-2-oxo-1-(phenylamino)nicotinonitrile

There total 28 articles about 1,2-Dihydro-6-hydroxy-4-methyl-2-oxo-1-(phenylamino)nicotinonitrile 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: 85.0%

2-phenylethynylaniline (13141-38-3) → 1-(2-aminophenyl)-2-phenylethanone (835-38-1)

Guidance literature:

With water; ammonium chloride; at 200 ℃; for 0.5h; Microwave irradiation;

DOI:10.1016/j.tet.2010.06.083

Reference yield: 82.0%

1-nitro-2-phenylethynyl-benzene (35010-17-4) → 1-(2-aminophenyl)-2-phenylethanone (835-38-1)

Guidance literature:

With hydrogenchloride; tin; sodiumsulfide nonahydrate; water; In ethanol; for 8h; Reflux;

DOI:10.3987/COM-09-11890

Reference yield: 78.0%

benzyl chloride (100-44-7) + anthranilic acid nitrile (1885-29-6) → 1-(2-aminophenyl)-2-phenylethanone (835-38-1)

Guidance literature:

benzyl chloride; With iodine; magnesium; In tetrahydrofuran; at 60 ℃; for 1.5h; Sealed tube;

anthranilic acid nitrile; In tetrahydrofuran; at 20 ℃; Sealed tube;

With hydrogenchloride; water; pH=1;

DOI:10.1021/acs.orglett.0c03011

upstream raw materials:

N-(2-(2-phenylacetyl)phenyl)acetamide

α-Phenyl-o-nitroacetophenone

anthranilic acid amide

benzylmagnesium chloride

Downstream raw materials:

2-Isothiocyanatodesoxybenzoin

ethyl 3-benzyl-1H-indole-2-carboxylate

[2-methyl-1-(2-phenylacetyl-phenylcarbamoyl)-propyl]-carbamic acid tert-butyl ester

[2-phenyl-1-(2-phenylacetyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Chang, Sukbok,Kim, Dongwook,Kim, Youyoung. "Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles". supporting information. p. 12309 - 12312. Retrieved 2021/12/07.
• 2、 Lee, Seok Beom,Jang, Yoonkyung,Ahn, Jiwon,Chun, Simin,Oh, Dong-Chan,Hong, Suckchang. "One-Pot Synthesis of 4-Quinolone via Iron-Catalyzed Oxidative Coupling of Alcohol and Methyl Arene". supporting information. p. 8382 - 8386. Retrieved 2020/11/18.