2,6-dimethyl-1-phenylpyridin-4(1H)-one

Base Information

• Chemical Name: 2,6-dimethyl-1-phenylpyridin-4(1H)-one
• CAS No.: 22192-08-1
• Molecular Formula: C13H13 N O
• Molecular Weight: 199.252
• Mol file: 22192-08-1.mol

Synonyms:4(1H)-Pyridone,2,6-dimethyl-1-phenyl- (7CI,8CI); NSC 87591

Chemical Property of 2,6-dimethyl-1-phenylpyridin-4(1H)-one

Chemical Property:

• Vapor Pressure: 0.00111mmHg at 25°C
• Boiling Point: 300.6°C at 760 mmHg
• Flash Point: 108.4°C
• Density: 1.102g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,6-dimethyl-1-phenylpyridin-4(1H)-one

There total 11 articles about 2,6-dimethyl-1-phenylpyridin-4(1H)-one 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: 98.0%

4-chloro-2,6-dimethyl-1(((trifluoromethyl)sulfonyl)oxy)pyridine-1-ium trifluoromethanesulfonate + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 2,6-dimethyl-1-phenylpyridin-4(1H)-one (22192-08-1)

Guidance literature:

4-chloro-2,6-dimethyl-1(((trifluoromethyl)sulfonyl)oxy)pyridine-1-ium trifluoromethanesulfonate; benzene; With C₁₀H₈N₂*Ru⁽²⁺⁾*2F₆P^(1-); In acetonitrile; at 23 - 25 ℃; for 24h; Sealed tube; Irradiation;

With tert.-butylhydroperoxide; water; sodium hydrogencarbonate; In tetrahydrofuran; at 0 ℃; for 0.666667h; Heating;

DOI:10.1021/acs.orglett.9b02054

Reference yield:

2,6-dimethyl-4-chloropyridine N-oxide (697-92-7) → 2,6-dimethyl-1-phenylpyridin-4(1H)-one (22192-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / -78 °C

2.1: C₁₀H₈N₂*Ru⁽²⁺⁾*2F₆P^(1-) / acetonitrile / 24 h / 23 - 25 °C / Sealed tube; Irradiation

2.2: 0.67 h / 0 °C / Heating

With C₁₀H₈N₂*Ru⁽²⁺⁾*2F₆P^(1-); In dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.9b02054

Reference yield:

4-chloro-2,6-lutidine (3512-75-2) → 2,6-dimethyl-1-phenylpyridin-4(1H)-one (22192-08-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 23 °C

2.1: dichloromethane / -78 °C

3.1: C₁₀H₈N₂*Ru⁽²⁺⁾*2F₆P^(1-) / acetonitrile / 24 h / 23 - 25 °C / Sealed tube; Irradiation

3.2: 0.67 h / 0 °C / Heating

With C₁₀H₈N₂*Ru⁽²⁺⁾*2F₆P^(1-); 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.9b02054

upstream raw materials:

tetrachloromethane

hepta-2,5-diyn-4-one

aniline

1,3-diacetyl acetone

Downstream raw materials:

2,6-dimethyl-1-phenyl-1H-pyridin-4-one-hydrazone; dihydrochloride

(2,6-dimethyl-1-phenyl-1H-[4]pyridylidene)-(4-nitro-benzylidene)-hydrazine

(2,6-dimethyl-1-phenyl-1H-[4]pyridyliden)-(4-oxo-4H-[1]naphthylidene)-hydrazine

benzoic acid-(2,6-dimethyl-1-phenyl-1H-[4]pyridylidenehydrazide)

Refernces

• 1、 Bartoli, Giuseppe,Bosco, Marcella,Cimarelli, Cristina,Dalpozzo, Renato,Guercio, Giuseppe,Palmieri, Gianni. "Reactions of Dianions of Acyclic β-Enamino Ketones with Electrophiles. Part 5. Esters: Synthesis of Pyridin-4-one and Pyran-4-one Derivatives". . p. 2081 - 2086. Retrieved 2007/10/02.