Methyl 6-chloro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate

Base Information

• Chemical Name: Methyl 6-chloro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate
• CAS No.: 123040-75-5
• Molecular Formula: C10H8ClNO4
• Molecular Weight: 241.631
• Hs Code.: 2934999090
• European Community (EC) Number: 602-915-6
• DSSTox Substance ID: DTXSID30563850
• Nikkaji Number: J1.627.606E
• Wikidata: Q72518499
• Mol file: 123040-75-5.mol

Synonyms:123040-75-5;Methyl 6-chloro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate;6-Chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid methyl ester;methyl 6-chloro-3-oxo-4H-1,4-benzoxazine-8-carboxylate;Methyl 6-chloro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate;GDSWKMQEDQRHLC-UHFFFAOYSA-N;SCHEMBL7281163;DTXSID30563850;BCP33663;methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate;AKOS015912032;Methyl 6-chloro-3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazine-8-carboxylate;2H-1,4-Benzoxazine-8-carboxylic acid, 6-chloro-3,4-dihydro-3-oxo-, methyl ester;AC-22836;A890860;J-004886;Methyl6-chloro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate

Chemical Property of Methyl 6-chloro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate

Chemical Property:

• Melting Point: 239-241 °C
• Boiling Point: 451.489 °C at 760 mmHg
• Flash Point: 226.853 °C
• PSA: 64.63000
• Density: 1.424 g/cm³
• LogP: 1.59550
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 241.0141854
• Heavy Atom Count: 16
• Complexity: 309

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C2C(=CC(=C1)Cl)NC(=O)CO2
• Uses: Intermediate in the preparation of Azasetron.

Technology Process of Methyl 6-chloro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate

There total 5 articles about Methyl 6-chloro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-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:

methyl 5-chloro-3-(chloroacetamido)-2-hydroxybenzoate → methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate (123040-75-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 2h; Yield given;

DOI:10.1248/cpb.40.624

Reference yield:

5-chloro-2-hydroxy-3-nitrobenzoic acid methyl ester (5043-79-8) → methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate (123040-75-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / 0.78N aq. NH₄Cl, Fe / toluene / 1 h / 85 - 90 °C

2: aq. NaHCO₃ / CHCl₃ / 2 h / 0 - 10 °C

3: K₂CO₃ / dimethylformamide / 2 h / 70 °C

With iron; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; In chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.40.624

Reference yield:

methyl 5-chloro-2-hydroxybenzoate (4068-78-4) → methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate (123040-75-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / HNO₃, conc. H₂SO₄ / 1 h / 0 - 5 °C

2: 79 percent / 0.78N aq. NH₄Cl, Fe / toluene / 1 h / 85 - 90 °C

3: aq. NaHCO₃ / CHCl₃ / 2 h / 0 - 10 °C

4: K₂CO₃ / dimethylformamide / 2 h / 70 °C

With sulfuric acid; nitric acid; iron; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; In chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.40.624

upstream raw materials:

methyl 5-chloro-2-hydroxybenzoate

3-amino-5-chloro-2-hydroxybenzoic acid methyl ester

5-chloro-2-hydroxy-3-nitrobenzoic acid methyl ester

C₁₂H₁₂ClNO₇

Downstream raw materials:

6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid

6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid chloride

4-Benzyl-6-chloro-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid

6-Chloro-3-oxo-4-phenethyl-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid

Refernces

• 1、 Kawakita,Kuroita,Yasumoto,Sano,Inaba,Fukuda,Tahara. "Synthesis and pharmacology of 3,4-dihydro-3-oxo-1,4-benzoxazine-8-carboxamide derivatives, a new class of potent serotonin-3 (5-HT3) receptor antagonists". . p. 624 - 630. Retrieved 2007/10/02.