Ethyl 2-methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate

Base Information

• Chemical Name: Ethyl 2-methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate
• CAS No.: 176383-20-3
• Molecular Formula: C15H16N2O5
• Molecular Weight: 304.302
• DSSTox Substance ID: DTXSID201136296
• Nikkaji Number: J1.406.709D
• Mol file: 176383-20-3.mol

Synonyms:176383-20-3;ethyl 2-methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate;3-Pyridinecarboxylic acid, 1,4,5,6-tetrahydro-2-methyl-4-(3-nitrophenyl)-6-oxo-, ethyl ester;Oprea1_022374;Oprea1_233153;DTXSID201136296;STK364288;AKOS000654959;AKOS021984676;UPCMLD0ENAT5974585:001;EU-0002458;VU0054355-2;AB00094779-01;SR-01000408225;SR-01000408225-1;Z57067439;F0265-1411;2-Methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydronicotinic acid ethyl ester;Ethyl 1,4,5,6-tetrahydro-2-methyl-4-(3-nitrophenyl)-6-oxo-3-pyridinecarboxylate;ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate

Chemical Property of Ethyl 2-methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 304.10592162
• Heavy Atom Count: 22
• Complexity: 509

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=O)CC1C2=CC(=CC=C2)[N+](=O)[O-])C

Technology Process of Ethyl 2-methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate

There total 1 articles about Ethyl 2-methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate 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: 65.0%

cycl-isopropylidene malonate (2033-24-1) + ethyl acetoacetate (141-97-9) + 3-nitro-benzaldehyde (99-61-6) → ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate (176383-20-3)

Guidance literature:

With ammonium acetate; acetic acid; for 10h; Heating;

DOI:10.1002/jhet.5570330118

Reference yield: 91.0%

ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate (176383-20-3) → ethyl 2-methyl-4-(3-nitrophenyl)-6-thioxo-1,4,5,6-tetrahydropyridine-3-carboxylate (1314745-75-9)

Guidance literature:

With Lawessons reagent; In 5,5-dimethyl-1,3-cyclohexadiene; at 60 ℃; for 0.166667h; regioselective reaction; Microwave irradiation;

DOI:10.3998/ark.5550190.0012.909

Reference yield: 88.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate (176383-20-3) → ethyl 6-chloro-5-formyl-2-methyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3-carboxylate (436849-88-6)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 5 ℃;

ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate; In chloroform; at 30 ℃; for 0.25h; Sonication;

With water; sodium acetate; In chloroform; at 20 ℃; for 0.166667h; Sonication;

DOI:10.1016/j.ultsonch.2011.07.003

upstream raw materials:

cycl-isopropylidene malonate

ethyl acetoacetate

3-nitro-benzaldehyde

Downstream raw materials:

ethyl 6-chloro-5-formyl-2-methyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

ethyl 2-methyl-4-(3-nitrophenyl)-6-thioxo-1,4,5,6-tetrahydropyridine-3-carboxylate