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

Base Information

• Chemical Name: Methyl 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate
• CAS No.: 141761-83-3
• Molecular Formula: C11H10ClNO4
• Molecular Weight: 255.658
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID40473799
• Nikkaji Number: J1.627.703G
• Wikidata: Q72518493
• Mol file: 141761-83-3.mol

Synonyms:141761-83-3;Methyl 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate;6-chloro-3,4-dihydro-4-methyl-3-oxo-2h-1,4-benzoxazine-8-carboxylic acid methyl ester;methyl 6-chloro-4-methyl-3-oxo-1,4-benzoxazine-8-carboxylate;2H-1,4-Benzoxazine-8-carboxylic acid, 6-chloro-3,4-dihydro-4-methyl-3-oxo-, methyl ester;6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylicAcid-13C,d3MethylEster;6-Chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylicAcid-d3MethylEster;DTXSID40473799;BCP14862;MFCD13185960;AKOS015908590;methyl 6-chloro-3,4-dihydro-4-methyl-3-oxo-2h-1,4-benzoxazine-8-carboxylate;DS-5556;CS-0151128;FT-0664635;C72643;A885560;Methyl 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate;Methyl6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate;Methyl 6-chloro-4-methyl-3-oxo-3 pound not4-dihydro-2H-benzo[b][1 pound not4]oxazine-8-carboxylate

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

Chemical Property:

• Vapor Pressure: 4.4E-10mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 498.8 °C at 760 mmHg
• PKA: -1.00±0.20(Predicted)
• Flash Point: 255.5 °C
• PSA: 55.84000
• Density: 1.384g/cm³
• LogP: 1.54680
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 255.0298355
• Heavy Atom Count: 17
• Complexity: 335

Purity/Quality:

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

6-Chloro-3,4-dihydro-4-methyl-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: CN1C(=O)COC2=C(C=C(C=C21)Cl)C(=O)OC
• Uses: Azasetron intermediate.

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

There total 6 articles about Methyl 6-chloro-4-methyl-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: 98.0%

methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate (123040-75-5) + methyl iodide (74-88-4) → 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester (141761-83-3)

Guidance literature:

methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate; With potassium carbonate; In d₇-N,N-dimethylformamide; at 55 ℃; for 1h;

methyl iodide; In water; N,N-dimethyl-formamide; at 55 ℃; for 1h; Concentration; Temperature;

Reference yield: 92.0%

3-amino-5-chloro-2-hydroxybenzoic acid methyl ester (5043-81-2) + chloroacetyl chloride (79-04-9) + carbonic acid dimethyl ester (616-38-6) → 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester (141761-83-3)

Guidance literature:

3-amino-5-chloro-2-hydroxybenzoic acid methyl ester; chloroacetyl chloride; With sodium hydrogencarbonate; In dichloromethane; at 0 ℃; for 3h;

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

carbonic acid dimethyl ester; In N,N-dimethyl-formamide; at 75 ℃; for 3h;

Reference yield:

methyl 5-chloro-2-hydroxybenzoate (4068-78-4) → 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester (141761-83-3)

Guidance literature:

Multi-step reaction with 5 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

5: 82.2 percent / K₂CO₃ / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h

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 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate

methyl iodide

methyl 5-chloro-2-hydroxybenzoate

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

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

azasetron

6-Chloro-4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (1-benzyl-piperidin-3-yl)-amide

Refernces

• 1、 -. "Novel preparation method of azasetron hydrochloride". . . Retrieved 2019/12/25.