Methyl 6-acetylpicolinate

Base Information

• Chemical Name: Methyl 6-acetylpicolinate
• CAS No.: 110144-24-6
• Molecular Formula: C9H9 N O3
• Molecular Weight: 179.175
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID60465030
• Wikidata: Q82290676
• Mol file: 110144-24-6.mol

Synonyms:Methyl 6-acetylpicolinate;110144-24-6;Methyl 6-acetylpyridine-2-carboxylate;6-ACETYL-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER;Methyl6-acetylpicolinate;SCHEMBL1829272;DTXSID60465030;AKOS006288567;SB53189;CS-0367434;EN300-153196;Z1198181830

Chemical Property of Methyl 6-acetylpicolinate

Chemical Property:

• Vapor Pressure: 0.000386mmHg at 25°C
• Melting Point: 64 °C
• Refractive Index: 1.518
• Boiling Point: 317.4°C at 760 mmHg
• PKA: 0.85±0.10(Predicted)
• Flash Point: 145.8°C
• PSA: 56.26000
• Density: 1.178g/cm³
• LogP: 1.07080
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 179.058243149
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

99% ^*data from raw suppliers

6-ACETYL-PYRIDINE-2-CARBOXYLICACIDMETHYLESTER 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=NC(=CC=C1)C(=O)OC

Technology Process of Methyl 6-acetylpicolinate

There total 6 articles about Methyl 6-acetylpicolinate 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: 47.0%

2,6-bis(methoxycarbonyl)pyridine (5453-67-8) + ethyl acetate (141-78-6) → Methyl 2-acetylpyridine-6-carboxlyate (110144-24-6)

Guidance literature:

2,6-bis(methoxycarbonyl)pyridine; ethyl acetate; With sodium methylate; In methanol; for 12h; Reflux; Inert atmosphere;

With hydrogenchloride; In methanol; water; for 6h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmcl.2014.07.085

Reference yield:

6-(methoxycarbonyl)pyridine-2-carboxylic acid (7170-36-7) → Methyl 2-acetylpyridine-6-carboxlyate (110144-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / benzene / 8 h / 50 °C

2: 1.4 M methyllithium / diethyl ether; tetrahydrofuran / 0.17 h

With thionyl chloride; methyllithium; In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1021/ja00290a027

Reference yield:

bis(trimethylsilyl) malonate (18457-04-0) + methyl 6-(chlorocarbonyl)picolinate (94111-79-2) → Methyl 2-acetylpyridine-6-carboxlyate (110144-24-6) + methyl 2-(carboxyacetyl)pyridine-6-carboxylate (94111-68-9)

Guidance literature:

With methyllithium; In tetrahydrofuran; diethyl ether; for 0.166667h; Yield given;

DOI:10.1021/ja00290a027

upstream raw materials:

6-(methoxycarbonyl)pyridine-2-carboxylic acid

lithium dimethylcuprate

bis(trimethylsilyl) malonate

methyl 6-(chlorocarbonyl)picolinate

Downstream raw materials:

1-(6-(hydroxymethyl)pyridin-2-yl)ethan-1-one

C₃₄H₂₄N₃O₄P

Methyl 8-(benzyloxy)-7-bromo-2-(2'-pyridyl)quinoline-6'-carboxylate

8-(Benzyloxy)-7-bromo-2-(2'-pyridyl)quinoline-6'-carboxylic acid

Refernces

• 1、 Boger, Dale L.,Yasuda, Masami,Mitscher, Lester A.,Drake, Steven D.,Kitos, Paul A.,Thompson, Sandra Collins. "Streptonigrin and Lavendamycin Partial Structures. Probes for the Minimum, Potent Pharmacophore of Streptonigrin, Lavendamycin, and Synthetic Quinoline-5,8-diones". . p. 1918 - 1928. Retrieved 2007/10/02.