ethyl 2-hydroxy-3-oxo-4H-1,4-benzoxazine-7-carboxylate

Base Information

• Chemical Name: ethyl 2-hydroxy-3-oxo-4H-1,4-benzoxazine-7-carboxylate
• CAS No.: 852233-79-5
• Molecular Formula: C₁₁H₁₁NO₅
• Molecular Weight: 237.212
• DSSTox Substance ID: DTXSID10462690
• Mol file: 852233-79-5.mol

Synonyms:ethyl 2-hydroxy-3-oxo-4H-1,4-benzoxazine-7-carboxylate;852233-79-5;SCHEMBL6471329;DTXSID10462690;AKOS015964259

Chemical Property of ethyl 2-hydroxy-3-oxo-4H-1,4-benzoxazine-7-carboxylate

Chemical Property:

• PSA: 88.35000
• LogP: 0.59770
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 237.06372245
• Heavy Atom Count: 17
• Complexity: 319

Purity/Quality:

2-HYDROXY-3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXAZINE-7-CARBOXYLIC ACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(C=C1)NC(=O)C(O2)O

Technology Process of ethyl 2-hydroxy-3-oxo-4H-1,4-benzoxazine-7-carboxylate

There total 4 articles about ethyl 2-hydroxy-3-oxo-4H-1,4-benzoxazine-7-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: 83.0%

ethyl 4-[(2,2-dichloroacetyl)amino]-3-hydroxybanzoate (852233-80-8) → ethyl 2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate (852233-79-5)

Guidance literature:

With sodium hydrogencarbonate; for 1h; Heating;

DOI:10.1021/jm048984g

Reference yield:

3-hydroxy-4-nitro-benzoic acid (619-14-7) → ethyl 2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate (852233-79-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / sulphuric acid / 2 h / Heating

2: 100 percent / H₂ / Pd/C / ethanol / 20 °C

3: 60 percent / triethylamine / diethyl ether / 5 h / -10 - 20 °C

4: 83 percent / aq. NaHCO₃ / 1 h / Heating

With sulfuric acid; hydrogen; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol;

DOI:10.1021/jm048984g

Reference yield:

ethyl 3-hydroxy-4-nitro-benzoate (717-01-1) → ethyl 2-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate (852233-79-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂ / Pd/C / ethanol / 20 °C

2: 60 percent / triethylamine / diethyl ether / 5 h / -10 - 20 °C

3: 83 percent / aq. NaHCO₃ / 1 h / Heating

With hydrogen; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol;

DOI:10.1021/jm048984g

upstream raw materials:

ethyl 4-[(2,2-dichloroacetyl)amino]-3-hydroxybanzoate

3-hydroxy-4-nitro-benzoic acid

ethyl 3-hydroxy-4-nitro-benzoate

ethyl 4-amino-3-hydroxybenzoate

Downstream raw materials:

ethyl (3S)-3-[({2-[(4-cyanobenzyl)oxo]-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-yl}carbonyl)amino]-3-phenylpropanoate

ethyl 2-[(4-cyanobenzyl)oxy]-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate

2-[(4-cyanobenzyl)oxy]-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylic acid