2-Amino-6,7-dimethoxyquinoline-3-carboxamide

Base Information

• Chemical Name: 2-Amino-6,7-dimethoxyquinoline-3-carboxamide
• CAS No.: 55149-43-4
• Molecular Formula: C12H13N3O3
• Molecular Weight: 247.25000
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID30354780
• Wikidata: Q82133190
• ChEMBL ID: CHEMBL1329224
• Mol file: 55149-43-4.mol

Synonyms:2-amino-6,7-dimethoxyquinoline-3-carboxamide;55149-43-4;2-Amino-6,7-dimethoxy-quinoline-3-carboxylic acid amide;MLS000532528;2-amino-6,7-dimethoxy-3-quinolinecarboxamide;SMR000137467;CBMicro_020449;Oprea1_235825;cid_781584;SCHEMBL8352155;CHEMBL1329224;BDBM74774;C20HF41O6;DTXSID30354780;AAZKQXRGMFBMCF-UHFFFAOYSA-N;HMS2190O18;CCG-8055;MFCD00815945;AKOS003238689;SB71209;AS-69932;BIM-0020182.P001;CS-0314701;6,7-Dimethoxy-2-Aminoquinoline-3-Carboxamide;2-amino-6,7-dimethoxy-quinoline-3-carboxamide;2-azanyl-6,7-dimethoxy-quinoline-3-carboxamide;SR-01000368745;SR-01000368745-1

Chemical Property of 2-Amino-6,7-dimethoxyquinoline-3-carboxamide

Chemical Property:

• PSA: 100.46000
• LogP: 2.21460
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 247.09569129
• Heavy Atom Count: 18
• Complexity: 313

Purity/Quality:

98.5% ^*data from raw suppliers

2-Amino-6,7-dimethoxyquinoline-3-carboxamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=CC(=C(N=C2C=C1OC)N)C(=O)N

Technology Process of 2-Amino-6,7-dimethoxyquinoline-3-carboxamide

There total 6 articles about 2-Amino-6,7-dimethoxyquinoline-3-carboxamide 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: 90.0%

6-nitroveratraldehyde (20357-25-9) + cyanoacetic acid amide (107-91-5) → 2-amino-6,7-dimethoxyquinoline-3-carboxamide (55149-43-4)

Guidance literature:

With ammonium chloride; zinc; In neat (no solvent); for 0.1h; Microwave irradiation;

DOI:10.1002/jhet.4203

Reference yield: 84.0%

α-cyano-β-(2-nitro-4,5-dimethoxyphenyl)acrylamide (55801-65-5) → 2-amino-6,7-dimethoxyquinoline-3-carboxamide (55149-43-4)

Guidance literature:

With iron; acetic acid; In N,N-dimethyl-formamide; at 90 ℃; for 4h;

DOI:10.1021/jm00177a010

Reference yield: 55.0%

2-bromo-4,5-dimethoxybenzaldehyde (5392-10-9) + cyanoacetic acid amide (107-91-5) → 2-amino-6,7-dimethoxyquinoline-3-carboxamide (55149-43-4)

Guidance literature:

With copper(l) iodide; sodium azide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 150 ℃; for 3h; regioselective reaction;

DOI:10.1039/c6ra03798d

upstream raw materials:

α-cyano-β-(2-nitro-4,5-dimethoxyphenyl)acrylamide

6-nitroveratraldehyde

iron

glacial acetic acid,dimethylformamide

Downstream raw materials:

ethyl 7,8-dimethoxy-3,4-dihydro-4-oxopyrimido<4,5-b>quinoline-2-carboxylate

Refernces

• 1、 Dhiman, Shiv,Saini, Hitesh Kumar,Nandwana, Nitesh Kumar,Kumar, Dalip,Kumar, Anil. "Copper-catalyzed synthesis of quinoline derivatives via tandem Knoevenagel condensation, amination and cyclization". . p. 23987 - 23994. Retrieved 2016/03/15.
• 2、 Althuis, T. H.,Kadin, S. B.,Czuba, L. J.,Moore, P. F.,Hess, H.-J.. "Structure-Activity Relationships in a Series of Novel 3,4-Dihydro-4-oxopyrimidoquinoline-2-carboxylic Acid Antiallergy Agents". . p. 262 - 269. Retrieved 2007/10/02.