2H-1,4-Benzoxazine-2-acetic acid, 7-[(4-cyanobenzoyl)amino]-3,4-dihydro-2,4-dimethyl-3-oxo-, methyl ester

Base Information

• Chemical Name: 2H-1,4-Benzoxazine-2-acetic acid, 7-[(4-cyanobenzoyl)amino]-3,4-dihydro-2,4-dimethyl-3-oxo-, methyl ester
• CAS No.: 847671-42-5
• Molecular Formula: C21H19N3O5
• Molecular Weight: 393.399
• Mol file: 847671-42-5.mol

Synonyms:

Chemical Property of 2H-1,4-Benzoxazine-2-acetic acid, 7-[(4-cyanobenzoyl)amino]-3,4-dihydro-2,4-dimethyl-3-oxo-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-1,4-Benzoxazine-2-acetic acid, 7-[(4-cyanobenzoyl)amino]-3,4-dihydro-2,4-dimethyl-3-oxo-, methyl ester

There total 7 articles about 2H-1,4-Benzoxazine-2-acetic acid, 7-[(4-cyanobenzoyl)amino]-3,4-dihydro-2,4-dimethyl-3-oxo-, methyl ester 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: 74.0%

4-cyanobenzoyl chlorIde (6068-72-0) + methyl 2-(7-amino-2,4-dimethyl-2H-1,4-benzoxazin-3(4H)-on-2-yl)acetate (847671-41-4) → methyl 2-{7-[(4-cyanobenzoyl)amino]-2,4-dimethyl-2H-1,4-benzoxazin-3(4H)-on-2-yl}acetate (847671-42-5)

Guidance literature:

With triethylamine; In dichloromethane; at -10 - 20 ℃; for 6h;

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) → 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:

2-(2-diazoacetyl)-2,4-dimethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one-2-carboxylic acid (386214-83-1) → 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 3 steps

1: 84 percent / silver benzoate; triethylamine / 0.5 h / ultrasound sonication

2: 95 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

3: 74 percent / triethylamine / CH₂Cl₂ / 6 h / -10 - 20 °C

With hydrogen; silver benzoate; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; 1: Wolff rearrangement;

DOI:10.1016/j.ejmech.2004.09.004

upstream raw materials:

4-cyanobenzoyl chlorIde

methyl 2-(7-amino-2,4-dimethyl-2H-1,4-benzoxazin-3(4H)-on-2-yl)acetate

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

2-(2-diazoacetyl)-2,4-dimethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one-2-carboxylic acid

Refernces