3-(2-Methyl-1,3-dioxolan-2-YL)-6-methylpyridine

Base Information

• Chemical Name: 3-(2-Methyl-1,3-dioxolan-2-YL)-6-methylpyridine
• CAS No.: 184766-45-8
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.22
• DSSTox Substance ID: DTXSID70400694
• Wikidata: Q82203710
• Mol file: 184766-45-8.mol

Synonyms:184766-45-8;3-(2-METHYL-1,3-DIOXOLAN-2-YL)-6-METHYLPYRIDINE;2-methyl-5-(2-methyl-1,3-dioxolan-2-yl)pyridine;Pyridine,2-methyl-5-(2-methyl-1,3-dioxolan-2-yl)-;DTXSID70400694;AKOS006286537;FT-0671706;3-(2-Methyl-1,3-dioxan-2-yl)-6-methylpyridine;W-201660

Chemical Property of 3-(2-Methyl-1,3-dioxolan-2-YL)-6-methylpyridine

Chemical Property:

• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 269.4ºC at 760 mmHg
• Flash Point: 98.7ºC
• PSA: 31.35000
• Density: 1.1g/cm3
• LogP: 1.60950
• Solubility.: Acetone, Chloroform, Dichloromethane, DMF, DMSO, Methanol
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 178

Purity/Quality:

99%min ^*data from raw suppliers

3-(2-Methyl-1,3-dioxolan-2-yl)-6-methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=C(C=C1)C2(OCCO2)C
• Uses: 3-(2-Methyl-1,3-dioxolan-2-yl)-6-methylpyridine is used in the synthesis and biological activity of metabolites of the antidiabetic, antihyperglycemic agent Pioglitazone (P471000).

Technology Process of 3-(2-Methyl-1,3-dioxolan-2-YL)-6-methylpyridine

There total 3 articles about 3-(2-Methyl-1,3-dioxolan-2-YL)-6-methylpyridine 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: 92.0%

1-(6-methyl-pyridin-3-yl)-ethanone (36357-38-7) + ethylene glycol (107-21-1) → 3-(2-methyl-1,3-dioxolan-2-yl)-6-methylpyridine (184766-45-8)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 8h; Heating;

DOI:10.1021/jm9605694

Reference yield:

Methyl 6-methylnicotinate (5470-70-2) → 3-(2-methyl-1,3-dioxolan-2-yl)-6-methylpyridine (184766-45-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / dimethylformamide; toluene / 2.5 h / 80 °C

2: 10percent aq. H₂SO₄ / 2 h / Heating

3: 92 percent / pTsOH / toluene / 8 h / Heating

With sulfuric acid; sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm9605694

Reference yield:

ethyl 3-(2-methyl-5-pyridinyl)-3-oxopropanoate (21683-58-9) → 3-(2-methyl-1,3-dioxolan-2-yl)-6-methylpyridine (184766-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 10percent aq. H₂SO₄ / 2 h / Heating

2: 92 percent / pTsOH / toluene / 8 h / Heating

With sulfuric acid; toluene-4-sulfonic acid; In toluene;

DOI:10.1021/jm9605694

upstream raw materials:

1-(6-methyl-pyridin-3-yl)-ethanone

ethylene glycol

Methyl 6-methylnicotinate

ethyl 3-(2-methyl-5-pyridinyl)-3-oxopropanoate

Downstream raw materials:

5-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-benzyl)-thiazolidine-2,4-dione

5-[1-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-phenyl)-meth-(Z)-ylidene]-thiazolidine-2,4-dione

4-{2-[5-(2-methyl-1,3-dioxolan-2-yl)-2-pyridyl]ethoxy}benzaldehyde

Ketopioglitazone

Refernces