Ethyl 2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Base Information

• Chemical Name: Ethyl 2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
• CAS No.: 154365-36-3
• Molecular Formula: C₁₂H₁₂N₂O₆
• Molecular Weight: 280.237
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID40446564
• Mol file: 154365-36-3.mol

Synonyms:154365-36-3;Ethyl 2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate;ethyl 2-methyl-7-nitro-3-oxo-4H-1,4-benzoxazine-2-carboxylate;Ethyl 2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate;Ethyl2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate;DTXSID40446564;MFCD08443980;AKOS005072087;Ethyl 3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylate;CA-0827;CS-0447261

Chemical Property of Ethyl 2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Chemical Property:

• Melting Point: 193-195°C
• Boiling Point: 457.9±45.0 °C(Predicted)
• PKA: 10.17±0.40(Predicted)
• PSA: 110.45000
• Density: 1.372±0.06 g/cm3(Predicted)
• 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-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl 2-methyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

There total 1 articles about Ethyl 2-methyl-7-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: 96.0%

diethyl bromomethylmalonate (29263-94-3) + 5-Nitro-2-aminophenol (121-88-0) → 3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid ethyl ester (154365-36-3)

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-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid ethyl ester (154365-36-3) → methyl 2-{7-[(4-cyanobenzoyl)amino]-2,4-dimethyl-2H-1,4-benzoxazin-3(4H)-on-2-yl}acetate (847671-42-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / KF / dimethylformamide / 20 - 60 °C

2.1: 94 percent / NaOH; HCl / dioxane; H₂O / 24 h / 20 °C

3.1: triethylamine; ethyl chloroformate / tetrahydrofuran / 0.5 h / -5 °C

3.2: 92 percent / tetrahydrofuran; acetonitrile; hexane / 24 h / 4 °C

4.1: 84 percent / silver benzoate; triethylamine / 0.5 h / ultrasound sonication

5.1: 95 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

6.1: 74 percent / triethylamine / CH₂Cl₂ / 6 h / -10 - 20 °C

With hydrogenchloride; potassium fluoride; sodium hydroxide; hydrogen; silver benzoate; chloroformic acid ethyl ester; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Wolff rearrangement;

DOI:10.1016/j.ejmech.2004.09.004

Reference yield:

3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid ethyl ester (154365-36-3) → {[7-(4-carbamimidoyl-benzoylamino)-2,4-dimethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-2-carbonyl]-amino}-acetic acid; compound with acetic acid

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / KF / dimethylformamide / 20 - 60 °C

2: 94 percent / NaOH; HCl / dioxane; H₂O / 24 h / 20 °C

3: 73 percent / N-ethyl-N'-(dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole monohydrate; N-methylmorpholine / dimethylformamide / -10 - 20 °C / pH 8

4: 98 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

5: 76 percent / triethylamine / CH₂Cl₂ / 6 h / -10 - 20 °C

6: 70 percent / hydroxylammonium chloride; triethylamine / ethanol / 50 °C

7: 57 percent / pyridine / 6 h / 120 °C

8: 99 percent / NaOH; acetic acid / ethanol; H₂O / 4 °C

9: 72 percent / H₂ / palladium on charcoal / dimethylformamide

With 4-methyl-morpholine; pyridine; hydrogenchloride; potassium fluoride; sodium hydroxide; hydroxylamine hydrochloride; hydrogen; acetic acid; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2004.09.004

upstream raw materials:

diethyl bromomethylmalonate

5-Nitro-2-aminophenol

Downstream raw materials:

3,4-dihydro-2-methyl-7-nitro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid

methyl 2-{7-[(4-cyanobenzoyl)amino]-2,4-dimethyl-2H-1,4-benzoxazin-3(4H)-on-2-yl}acetate

ethyl 7-[(4-cyanobenzoyl)amino]-2-methyl-2H-1,4-benzoxazin-3(4H)-one-2-carboxylate

ethyl (2S)-2-{[(7-amino-2-methyl-2H-1,4-benzoxazin-3(4H)-on-2-yl)carbonyl]amino}-3-phenylpropanoate

Refernces

• 1、 Ilic, Milos,Kontogiorgis, Christos,Hadjipavlou-Litina, Dimitra,Ilas, Janez,Kikelj, Danijel. "Thrombin inhibitors with lipid peroxidation and lipoxygenase inhibitory activities". scheme or table. p. 4705 - 4709. Retrieved 2011/09/20.
• 2、 Anderluh, Marko,Cesar, Jǒko,?tefanǐ, Petra,Kikelj, Danijel,Janě, Damjan,Murn, Jernej,Nadrah, Kristina,Tominc, Mojca,Addicks, Elisabeth,Giannis, Athanassios,Stegnar, Mojca,Dolenc, Marija Sollner. "Design and synthesis of novel platelet fibrinogen receptor antagonists with 2H-1,4-benzoxazine-3(4H)-one scaffold. A systematic study". . p. 25 - 49. Retrieved 2007/10/03.