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

Base Information

• Chemical Name: methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate
• CAS No.: 202195-67-3
• Molecular Formula: C₁₀H₉NO₄
• Molecular Weight: 207.186
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10388043
• Wikidata: Q72494177
• Mol file: 202195-67-3.mol

Synonyms:202195-67-3;methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate;methyl 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate;methyl 3-oxo-4H-1,4-benzoxazine-6-carboxylate;2H-1,4-BENZOXAZINE-6-CARBOXYLIC ACID, 3,4-DIHYDRO-3-OXO-, METHYL ESTER;MFCD03036646;METHYL 3,4-DIHYDRO-3-OXO-2H-BENZO[B][1,4]OXAZINE-6-CARBOXYLATE;SCHEMBL6752;TimTec1_002821;Oprea1_205993;AMY4863;DTXSID10388043;WPGYGHFVLMZWHI-UHFFFAOYSA-N;3,4-Dihydro-6-(methoxycarbonyl)-3-oxo-2H-1,4-benzoxazine;HMS1542A05;HMS3507B20;BCP33515;METHYL3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXAZINE-6-CARBOXYLATE;STK735133;AKOS001146863;CCG-185198;HA-0820;MB02575;3-OXO-3,4-DIHYDRO-2H-BENZO[1,4]OXAZINE-6-CARBOXYLIC ACID METHYL ESTER;SY008771;CS-0094389;FT-0732604;methyl 1,4-benzoxazine-3-one-6-carboxylate;A879774;SR-01000536972;J-522206;SR-01000536972-1;BRD-K97568940-001-01-6;Z57473907;methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carboxylate;methyl 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate;methyl3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylate;3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-carboxylic acid methyl ester

Chemical Property of methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

Chemical Property:

• Melting Point: 183-185 °C
• Boiling Point: 412.1 °C at 760 mmHg
• PKA: 12.05±0.20(Predicted)
• Flash Point: 203.1 °C
• PSA: 64.63000
• Density: 1.313 g/cm³
• LogP: 0.94210
• Storage Temp.: 2-8°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 207.05315777
• Heavy Atom Count: 15
• Complexity: 279

Purity/Quality:

98%min ^*data from raw suppliers

Methyl3-Oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1)OCC(=O)N2

Technology Process of methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

There total 23 articles about methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-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: 84.0%

methyl (4-hydroxy-3-nitro)benzoate (99-42-3) + ethyl bromoacetate (105-36-2) → methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (604756-32-3,202195-67-3)

Guidance literature:

methyl (4-hydroxy-3-nitro)benzoate; ethyl bromoacetate; With potassium carbonate; In acetone; at 55 ℃; for 18h;

With iron; acetic acid; at 117 ℃; for 5.5h;

Reference yield: 83.0%

chloroacetyl chloride (79-04-9) + methyl 3-amino-4-hydroxybenzoate (536-25-4) → methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (604756-32-3,202195-67-3)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; In chloroform; at 55 ℃; for 16h;

Reference yield: 75.0%

methyl 4-(2-ethoxy-2-oxoethoxy)-3-nitrobenzoate (873852-15-4) → methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (604756-32-3,202195-67-3)

Guidance literature:

With iron; acetic acid; at 70 ℃;

DOI:10.1016/j.bmcl.2016.02.009

upstream raw materials:

methanol

6-Carboxy-2,3-dihydro-3-oxo-4H-1,4-benzoxazine

3-amino-4-carbamoylmethoxy-benzoic acid methyl ester

3-(2-chloro-acetylamino)-4-hydroxy-benzoic acid methyl ester

Downstream raw materials:

6-Carboxy-2,3-dihydro-3-oxo-4H-1,4-benzoxazine

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

(3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-methanol

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

Refernces

• 1、 -. "QUINAZOLINE HETEROCYCLIC COMPOUND AS EGFR KINASE INHIBITOR AND PREPARATION AND APPLICATION THEREOF". . . Retrieved 2018/01/19.
• 2、 Geng, Bolin,Comita-Prevoir, Janelle,Eyermann, Charles J.,Reck, Folkert,Fisher, Stewart. "Exploring Left-Hand-Side substitutions in the benzoxazinone series of 4-amino-piperidine bacterial type IIa topoisomerase inhibitors". scheme or table. p. 5432 - 5435. Retrieved 2011/10/12.