Quinazoline-2-carboxylic acid

Base Information

• Chemical Name: Quinazoline-2-carboxylic acid
• CAS No.: 568630-14-8
• Molecular Formula: C9H6N2O2
• Molecular Weight: 174.158
• DSSTox Substance ID: DTXSID20597321
• Wikidata: Q82492847
• Mol file: 568630-14-8.mol

Synonyms:Quinazoline-2-carboxylic acid;568630-14-8;MFCD11870788;Chinazolincarbonsaure;Quinazoline-2-carboxylicacid;SCHEMBL2337793;DTXSID20597321;OKXPYKHKJCATPX-UHFFFAOYSA-N;AKOS022710040;AS-83143;SY029484;DB-027078;CS-0453795;C16002

Chemical Property of Quinazoline-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.697
• Boiling Point: 441.877 °C at 760 mmHg
• PKA: 6.04±0.39(Predicted)
• Flash Point: 221.04 °C
• PSA: 63.08000
• Density: 1.421 g/cm³
• LogP: 1.32800
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 174.042927438
• Heavy Atom Count: 13
• Complexity: 208

Purity/Quality:

99% ^*data from raw suppliers

Quinazoline-2-carboxylicAcid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=NC(=N2)C(=O)O

Technology Process of Quinazoline-2-carboxylic acid

There total 4 articles about Quinazoline-2-carboxylic acid 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: 93.0%

ethyl quinazoline-2-carboxylate (869299-42-3) → quinazoline-2-carboxylic acid (568630-14-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2013.07.043

Reference yield:

ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate (29113-33-5) → quinazoline-2-carboxylic acid (568630-14-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,N-dimethyl-formamide; thionyl chloride / chloroform / 4.5 h / Reflux

2.1: triethylamine; palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C / 775.74 Torr

2.2: 3 h / Reflux

3.1: sodium hydroxide / methanol / 1 h / 20 °C

With thionyl chloride; palladium 10% on activated carbon; hydrogen; triethylamine; N,N-dimethyl-formamide; sodium hydroxide; In methanol; ethanol; chloroform;

DOI:10.1016/j.bmcl.2013.07.043

Reference yield:

ethyl 4-chloro-quinazoline-2-carboxylate (34632-69-4) → quinazoline-2-carboxylic acid (568630-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C / 775.74 Torr

1.2: 3 h / Reflux

2.1: sodium hydroxide / methanol / 1 h / 20 °C

With palladium 10% on activated carbon; hydrogen; triethylamine; sodium hydroxide; In methanol; ethanol;

DOI:10.1016/j.bmcl.2013.07.043

upstream raw materials:

2-methylquinazoline

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

ethyl 4-chloro-quinazoline-2-carboxylate

ethyl quinazoline-2-carboxylate

Refernces

• 1、 Yuan, Yunyun,Elbegdorj, Orgil,Beletskaya, Irina O.,Selley, Dana E.,Zhang, Yan. "Structure activity relationship studies of 17-cyclopropylmethyl-3,14β- dihydroxy-4,5α-epoxy-6α-(isoquinoline-3′-carboxamido) morphinan (NAQ) analogues as potent opioid receptor ligands: Preliminary results on the role of electronic characteristics for affinity and function". . p. 5045 - 5048. Retrieved 2013/09/12.