3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

Base Information

• Chemical Name: 3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid
• CAS No.: 1064077-28-6
• Molecular Formula: C₁₄H₁₃NO₄
• Molecular Weight: 259.262
• Mol file: 1064077-28-6.mol

Synonyms:3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

Chemical Property of 3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

There total 6 articles about 3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 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: 69.0%

3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (216581-47-4) → 3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid (1064077-28-6)

Guidance literature:

With ammonium hydroxide; In methanol; water; at 75 ℃; for 18 - 24h;

DOI:10.1021/acs.jmedchem.8b01363

Reference yield:

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7) → 3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid (1064077-28-6)

Guidance literature:

Multi-step reaction with 6 steps

1: thionyl chloride / dichloromethane / 6 - 8 h / 20 °C / Inert atmosphere

2: zinc; hydrogenchloride / water / 4 - 6 h

3: sodium hydroxide / water; methanol / 19.5 h / 0 - 20 °C

4: tetrabutyl-ammonium chloride / water; methanol / 40 - 70 °C

5: tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium iodide; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water; dichloromethane / 3 h / 7 °C / Cooling with ice

6: ammonium hydroxide / water; methanol / 18 - 24 h / 75 °C

With hydrogenchloride; ammonium hydroxide; sodium hypochlorite; thionyl chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium iodide; sodium hydroxide; zinc; In methanol; dichloromethane; water;

DOI:10.1021/acs.jmedchem.8b01363

Reference yield:

2-hydroxymethyl-3-hydroxy-6-methyl-pyran-4(1H)-one (22639-17-4) → 3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid (1064077-28-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutyl-ammonium chloride / water; methanol / 40 - 70 °C

2: tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium iodide; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water; dichloromethane / 3 h / 7 °C / Cooling with ice

3: ammonium hydroxide / water; methanol / 18 - 24 h / 75 °C

With ammonium hydroxide; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium iodide; In methanol; dichloromethane; water;

DOI:10.1021/acs.jmedchem.8b01363

upstream raw materials:

3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

allomaltol

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

chlorokojic acid

Downstream raw materials:

5-(benzyloxy)-2-methylpyridin-4(1H)-one