Ethyl 6-(hydroxy(oxido)amino)-2-oxo-2H-chromene-3-carboxylate

Base Information

• Chemical Name: Ethyl 6-(hydroxy(oxido)amino)-2-oxo-2H-chromene-3-carboxylate
• CAS No.: 13373-28-9
• Molecular Formula: C12H9 N O6
• Molecular Weight: 263.207
• Hs Code.: 2932209090
• Mol file: 13373-28-9.mol

Synonyms:6-Nitro-2-oxo-2H-1-benzopyran-3-carboxylicacid ethyl ester; NSC 66338

Chemical Property of Ethyl 6-(hydroxy(oxido)amino)-2-oxo-2H-chromene-3-carboxylate

Chemical Property:

• Vapor Pressure: 1.05E-08mmHg at 25°C
• Melting Point: 198-199.5 °C
• Boiling Point: 461.7°Cat760mmHg
• Flash Point: 221°C
• PSA: 102.33000
• Density: 1.453g/cm³
• LogP: 2.40110

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethyl 6-(hydroxy(oxido)amino)-2-oxo-2H-chromene-3-carboxylate

There total 12 articles about Ethyl 6-(hydroxy(oxido)amino)-2-oxo-2H-chromene-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: 95.0%

5-Nitrosalicylaldehyde (97-51-8) + diethyl malonate (105-53-3) → ethyl 6-nitrobenzo-2-pyrone-3-carboxylate (13373-28-9)

Guidance literature:

With iron(III) chloride; N-fluorobis(benzenesulfon)imide; In neat (no solvent); at 80 ℃; for 48h; Inert atmosphere; Green chemistry;

DOI:10.1134/S1070428019070236

Reference yield: 89.0%

cycl-isopropylidene malonate (2033-24-1) + ethanol (64-17-5) + 5-Nitrosalicylaldehyde (97-51-8) → ethyl 6-nitrobenzo-2-pyrone-3-carboxylate (13373-28-9)

Guidance literature:

With iron(III) chloride; at 70 ℃; for 8h;

DOI:10.1016/j.tet.2014.12.042

Reference yield: 86.0%

ethyl coumarin-3-carboxylate (1846-76-0) → ethyl 6-nitrobenzo-2-pyrone-3-carboxylate (13373-28-9)

Guidance literature:

With nitric acid; acetic acid; for 3h; Reflux;

DOI:10.3184/174751913X13738962423671

upstream raw materials:

ethanol

6-nitro-2-oxo-2H-chromen-3-carboxylic acid

5-Nitrosalicylaldehyde

diethyl malonate

Downstream raw materials:

6-nitro-2-oxo-N-o-tolyl-2H-chromene-3-carboxamide

N-(2-methoxyphenyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide

6-nitro-2-oxo-N-m-tolyl-2H-chromene-3-carboxamide

6-nitro-2-oxo-N-(3-(trifluoromethyl)phenyl)-2H-chromene-3-carboxamide

Refernces

• 1、 You, Xinwen,Yu, Hua,Wang, Mangang,Wu, Jun,Shang, Zhicai. "A green method for the synthesis of 3-substituted coumarins catalyzed by L-lysine in water via knoevenagel condensation". . p. 19 - 23. Retrieved 2012.
• 2、 Asadipour, Ali,Alipour, Masoumeh,Jafari, Mona,Khoobi, Mehdi,Emami, Saeed,Nadri, Hamid,Sakhteman, Amirhossein,Moradi, Alireza,Sheibani, Vahid,Homayouni Moghadam, Farshad,Shafiee, Abbas,Foroumadi, Alireza. "Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors". . p. 623 - 630. Retrieved 2013.
• 3、 Balalaie, Saeed,Nemati, Navid. "One-pot preparation of coumarins by Knoevenagel condensation in solvent-free condition under microwave irradiation". . p. 67 - 72. Retrieved 2001.
• 4、 Bekhradnia, Ahmadreza,Domehri, Elham,Khosravi, Masome. "Novel coumarin-based fluorescent probe for selective detection of Cu(II)". . p. 18 - 22. Retrieved 2016.
• 5、 Ivanov,Raev. "Michael adducts from 6-nitrocoumarins and enaminoesters". . p. 53 - 58. Retrieved 1995.