2-Methoxy-4-(1-methoxyvinyl)-6-methyl-3-nitropyridine

Base Information

• Chemical Name: 2-Methoxy-4-(1-methoxyvinyl)-6-methyl-3-nitropyridine
• CAS No.: 221349-77-5
• Molecular Formula: C₁₀H₁₂N₂O₅
• Molecular Weight: 240.216
• DSSTox Substance ID: DTXSID30698611
• Wikidata: Q82628932
• Mol file: 221349-77-5.mol

Synonyms:221349-77-5;2-METHOXY-4-(1-METHOXYVINYL)-6-METHYL-3-NITROPYRIDINE;2-methoxy-4-(1-methoxyethenyl)-6-methyl-3-nitropyridine;DTXSID30698611;AKOS015966307

Chemical Property of 2-Methoxy-4-(1-methoxyvinyl)-6-methyl-3-nitropyridine

Chemical Property:

• Vapor Pressure: 6.89E-05mmHg at 25°C
• Boiling Point: 354.3°C at 760 mmHg
• Flash Point: 168.1°C
• PSA: 77.17000
• Density: 1.199g/cm³
• LogP: 2.44710
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 224.07970687
• Heavy Atom Count: 16
• Complexity: 277

Purity/Quality:

2-METHOXY-4-(1-METHOXYVINYL)-6-METHYL-3-NITROPYRIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=N1)OC)[N+](=O)[O-])C(=C)OC

Technology Process of 2-Methoxy-4-(1-methoxyvinyl)-6-methyl-3-nitropyridine

There total 2 articles about 2-Methoxy-4-(1-methoxyvinyl)-6-methyl-3-nitropyridine 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: 95.0%

trimethoxonium tetrafluoroborate (420-37-1) + ethyl 6-methyl-3-nitro-2-oxo-1,2-dihydropyridine-4-carboxylate (70026-89-0) → ethyl 2-methoxy-6-methyl-3-nitropyridine 4-carboxylate (221349-77-5)

Guidance literature:

In dichloromethane; Heating;

DOI:10.1016/S0960-894X(00)00170-0

Reference yield:

ethyl 6-methyl-3-nitro-2-oxo-1,2-dihydropyridine-4-carboxylate (70026-89-0) → ethyl 2-methoxy-6-methyl-3-nitropyridine 4-carboxylate (221349-77-5)

Guidance literature:

With trimethoxonium tetrafluoroborate; In dichloromethane; at 40 ℃; for 24 - 72h;

Reference yield:

ethyl 2-methoxy-6-methyl-3-nitropyridine 4-carboxylate (221349-77-5) → (6-methyl-2,8-dioxo-2,3,4,8-tetrahydro-1H-[1,7]naphthyridin-7-yl)-acetic acid benzyl ester (287920-42-7)

Guidance literature:

Multi-step reaction with 6 steps

1: Dibal-H / CH₂Cl₂

2: (COCl)2; DMSO; Et₃N

3: NaH / tetrahydrofuran

4: H₂ / Pd/C / methanol / 55 °C

5: pyridinium hydrochloride / 0.08 h / 155 °C

6: Cs₂CO₃ / dimethylformamide

With oxalyl dichloride; hydrogen; pyridine hydrochloride; sodium hydride; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Oxidation / 3: Horner-Emmons reaction / 4: Reduction / 5: deprotection / 6: Alkylation;

DOI:10.1016/S0960-894X(00)00170-0

upstream raw materials:

trimethoxonium tetrafluoroborate

ethyl 6-methyl-3-nitro-2-oxo-1,2-dihydropyridine-4-carboxylate

Downstream raw materials:

2-methoxy-6-methyl-3-nitro-pyridine-4-carbaldehyde

3-benzyl-6-methyl-1,3,4,7-tetrahydro-[1,7]naphthyridine-2,8-dione

3-benzyl-8-methoxy-6-methyl-3,4-dihydro-1H-[1,7]naphthyridin-2-one

(E)-2-Benzyl-3-(2-methoxy-6-methyl-3-nitro-pyridin-4-yl)-acrylic acid methyl ester