Ethyl 2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Base Information

• Chemical Name: Ethyl 2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
• CAS No.: 154365-37-4
• Molecular Formula: C12H12N2O6
• Molecular Weight: 280.23300
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80443512
• Mol file: 154365-37-4.mol

Synonyms:154365-37-4;Ethyl 2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate;Ethyl 3,4-dihydro-2-methyl-6-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylate;Ethyl 2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate;ethyl 2-methyl-6-nitro-3-oxo-4H-1,4-benzoxazine-2-carboxylate;SCHEMBL2104226;DTXSID80443512;RARDOKXXQXTSKH-UHFFFAOYSA-N;MFCD08443979;AKOS005072086;CA-0826;CS-0320891;J-520773;Ethyl2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate

Chemical Property of Ethyl 2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Chemical Property:

• PSA: 110.45000
• LogP: 1.90870
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 280.06953611
• Heavy Atom Count: 20
• Complexity: 434

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl2-Methyl-6-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(C(=O)NC2=C(O1)C=CC(=C2)[N+](=O)[O-])C

Technology Process of Ethyl 2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

There total 2 articles about Ethyl 2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-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: 79.0%

diethyl bromomethylmalonate (29263-94-3) + 2-hydroxy-5-nitroaniline (99-57-0) → 3,4-dihydro-2-methyl-6-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid ethyl ester (154365-37-4)

Guidance literature:

With potassium fluoride; In N,N-dimethyl-formamide; for 16h;

DOI:10.1248/cpb.48.428

Reference yield:

diethyl bromomethylmalonate (29263-94-3) + 2-hydroxy-5-nitroaniline (99-57-0) → 3,4-dihydro-2-methyl-6-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid ethyl ester (154365-37-4) + 2-<2'-(1,1-bisethoxycarbonylethylamino)-4'-nitrophenoxy>-2-methylmalonic acid diethyl ester

Guidance literature:

With potassium fluoride; In N,N-dimethyl-formamide; at 60 ℃; for 6h;

DOI:10.1002/jhet.5570300303

Reference yield:

3,4-dihydro-2-methyl-6-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid ethyl ester (154365-37-4) → ethyl 6-[(4-cyanobenzoyl)amino]-2,4-dimethyl-2H-1,4-benzoxazin-3(4H)-one-2-carboxylate (847671-17-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 36 percent / NaH / toluene / 100 °C

2: 72 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

3: 83 percent / triethylamine / CH₂Cl₂ / 6 h / -10 - 20 °C

With hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; toluene;

DOI:10.1016/j.ejmech.2004.09.004

upstream raw materials:

diethyl bromomethylmalonate

2-hydroxy-5-nitroaniline

Downstream raw materials:

3,4-dihydro-2-methyl-6-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid

ethyl 6-amino-2,4-dimethyl-2H-1,4-benzoxazin-3(4H)-one-2-carboxylate

ethyl 6-amino-4-benzyl-2-methyl-2H-1,4-benzoxazin-3(4H)-one-2-carboxylate

ethyl 6-[(4-cyanobenzoyl)amino]-2-methyl-2H-1,4-benzoxazin-3(4H)-one-2-carboxylate