3-Hydroxy-1-methyl-4-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1,6-dihydro-pyridine-2,5-dione

Base Information

• Chemical Name: 3-Hydroxy-1-methyl-4-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1,6-dihydro-pyridine-2,5-dione
• CAS No.: 299957-21-4
• Molecular Formula: C₁₉H₁₅NO₃
• Molecular Weight: 305.333
• Mol file: 299957-21-4.mol

Synonyms:3-Hydroxy-1-methyl-4-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1,6-dihydro-pyridine-2,5-dione

Chemical Property of 3-Hydroxy-1-methyl-4-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1,6-dihydro-pyridine-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Hydroxy-1-methyl-4-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1,6-dihydro-pyridine-2,5-dione

There total 3 articles about 3-Hydroxy-1-methyl-4-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1,6-dihydro-pyridine-2,5-dione 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: 35.0%

(Z)-5-benzylidene-2,4-dioxo-1-methyl-pyrrolidine-3,3'-spiro-2'-phenyloxirane (299957-31-6) → 3-Hydroxy-1-methyl-4-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1,6-dihydro-pyridine-2,5-dione (299957-21-4)

Guidance literature:

With triethyloxonium fluoroborate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/1521-4184(20007)333:7<211::AID-ARDP211>3.0.CO;2-9

Reference yield:

3,5-Bis-benzyliden-pyrrolidin-2,4-dion (108045-40-5) → 3-Hydroxy-1-methyl-4-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1,6-dihydro-pyridine-2,5-dione (299957-21-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 70 percent / H₂O₂; aq. NaOH / methanol / 0.5 h

2.1: NaH / dimethylformamide / 0.5 h / 20 °C

2.2: 65 percent / dimethylformamide / 1 h

3.1: 35 percent / Et₃O(+)BF₄(-) / CH₂Cl₂ / 24 h / 20 °C

With sodium hydroxide; dihydrogen peroxide; triethyloxonium fluoroborate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Epoxidation / 2.1: deprotonation / 2.2: Methylation / 3.1: Rearrangement;

DOI:10.1002/1521-4184(20007)333:7<211::AID-ARDP211>3.0.CO;2-9

Reference yield:

2-Phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1-oxa-5-aza-spiro[2.4]heptane-4,7-dione (299957-27-0) → 3-Hydroxy-1-methyl-4-phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1,6-dihydro-pyridine-2,5-dione (299957-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 0.5 h / 20 °C

1.2: 65 percent / dimethylformamide / 1 h

2.1: 35 percent / Et₃O(+)BF₄(-) / CH₂Cl₂ / 24 h / 20 °C

With triethyloxonium fluoroborate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; 1.1: deprotonation / 1.2: Methylation / 2.1: Rearrangement;

DOI:10.1002/1521-4184(20007)333:7<211::AID-ARDP211>3.0.CO;2-9

upstream raw materials:

(Z)-5-benzylidene-2,4-dioxo-1-methyl-pyrrolidine-3,3'-spiro-2'-phenyloxirane

3,5-Bis-benzyliden-pyrrolidin-2,4-dion

2-Phenyl-6-[1-phenyl-meth-(Z)-ylidene]-1-oxa-5-aza-spiro[2.4]heptane-4,7-dione

Downstream raw materials:

(Z)-6-benzylidene-3-methoxy-4-phenyl-1-methyl-1,2,5,6-tetrahydropyridine-2,5-dione