Ethyl 4-chloroquinazoline-2-carboxylate

Base Information

• Chemical Name: Ethyl 4-chloroquinazoline-2-carboxylate
• CAS No.: 34632-69-4
• Molecular Formula: C11H9ClN2O2
• Molecular Weight: 236.658
• Hs Code.: 2933990090
• European Community (EC) Number: 822-086-6
• DSSTox Substance ID: DTXSID20392838
• Wikidata: Q72473807
• Mol file: 34632-69-4.mol

Synonyms:Ethyl 4-chloroquinazoline-2-carboxylate;34632-69-4;ETHYL 4-CHLORO-2-QUINAZOLINECARBOXYLATE;MFCD04107645;2-QUINAZOLINECARBOXYLIC ACID, 4-CHLORO-, ETHYL ESTER;SCHEMBL161315;DTXSID20392838;ZMAJSODACDWUAS-UHFFFAOYSA-N;2-ethoxycarbonyl-4-chloroquinazoline;AC2318;AKOS005067022;AB17516;MS-1837;AC-26858;SY005039;CS-0041693;FT-0645523;EN300-62924;(S)-3-Amino-3-(3-chloro-phenyl)-propionicacid;A849484;J-521001;Z988984042

Chemical Property of Ethyl 4-chloroquinazoline-2-carboxylate

Chemical Property:

• Vapor Pressure: 2.49E-06mmHg at 25°C
• Melting Point: 100-101 °C
• Refractive Index: 1.615
• Boiling Point: 391.3 °C at 760 mmHg
• PKA: -0.74±0.30(Predicted)
• Flash Point: 190.5 °C
• PSA: 52.08000
• Density: 1.342 g/cm³
• LogP: 2.45990
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 236.0352552
• Heavy Atom Count: 16
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

Ethyl4-Chloroquinazoline-2-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: CCOC(=O)C1=NC2=CC=CC=C2C(=N1)Cl
• Uses: Ethyl 4-Chloroquinazoline-2-carboxylate is a reactant used in the synthesis and evaluation of novel quinazoline-based anti-inflammatory agents acting as PDE4B inhibitors.

Technology Process of Ethyl 4-chloroquinazoline-2-carboxylate

There total 5 articles about Ethyl 4-chloroquinazoline-2-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: 97.0%

ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate (29113-33-5) → ethyl 4-chloro-quinazoline-2-carboxylate (34632-69-4)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In chloroform; for 4.5h; Reflux;

DOI:10.1016/j.bmcl.2013.07.043

Reference yield:

anthranilic acid amide (28144-70-9,88-68-6) → ethyl 4-chloro-quinazoline-2-carboxylate (34632-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 6 h / Reflux

2: trichlorophosphate / benzene / 6 h / Reflux

With trichlorophosphate; In benzene;

DOI:10.1248/cpb.c14-00737

Reference yield:

2-carbamoyloxanilic acid ethyl ester (54166-94-8) → ethyl 4-chloro-quinazoline-2-carboxylate (34632-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate / ethanol / 0 - 20 °C

2: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / Reflux

With sodium methylate; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In ethanol; toluene;

DOI:10.1016/j.bioorg.2018.10.027

upstream raw materials:

ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate

anthranilic acid amide

2-carbamoyloxanilic acid ethyl ester

Downstream raw materials:

(2-methoxyphenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone

(4-chloroquinazolin-2-yl)(3,4-difluorophenyl)methanone

(S)-(4-fluorophenyl)(4-((5-methyl-1H-pyrazol-3-yl)amino)quinazolin-2-yl)methanol

(S)-(4-fluorophenyl)(4-((5-methyl-1H-pyrazol-3-yl)amino)quinazolin-2-yl)methanol hydrochloride

Refernces

• 1、 Fan, Zhijiang,Shi, Jun,Luo, Na,Ding, Muhan,Bao, Xiaoping. "Synthesis, Crystal Structure, and Agricultural Antimicrobial Evaluation of Novel Quinazoline Thioether Derivatives Incorporating the 1,2,4-Triazolo[4,3- a]pyridine Moiety". . p. 11598 - 11606. Retrieved 2019/10/19.
• 2、 Yuan, Yunyun,Zaidi, Saheem A.,Stevens, David L.,Scoggins, Krista L.,Mosier, Philip D.,Kellogg, Glen E.,Dewey, William L.,Selley, Dana E.,Zhang, Yan. "Design, syntheses, and pharmacological characterization of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3′-carboxamido)morphinan analogues as opioid receptor ligands". supporting information. p. 1701 - 1715. Retrieved 2015/03/30.