4-HYDROXY-1-METHYL-2-OXO-1,2-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID (2-AMINO-PHENYL)-AMIDE

Base Information

• Chemical Name: 4-HYDROXY-1-METHYL-2-OXO-1,2-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID (2-AMINO-PHENYL)-AMIDE
• CAS No.: 151449-78-4
• Molecular Formula: C17H15 N3 O3
• Molecular Weight: 309.32
• Mol file: 151449-78-4.mol

Synonyms:4-HYDROXY-1-METHYL-2-OXO-1,2-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID (2-AMINO-PHENYL)-AMIDE;4-Hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (2-aminopheyl)ami

Chemical Property of 4-HYDROXY-1-METHYL-2-OXO-1,2-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID (2-AMINO-PHENYL)-AMIDE

Chemical Property:

• Vapor Pressure: 7.85E-12mmHg at 25°C
• Boiling Point: 524.6°C at 760 mmHg
• Flash Point: 271°C
• Density: 1.466g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

4-Hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (2-aminopheyl)amide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-HYDROXY-1-METHYL-2-OXO-1,2-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID (2-AMINO-PHENYL)-AMIDE

There total 3 articles about 4-HYDROXY-1-METHYL-2-OXO-1,2-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID (2-AMINO-PHENYL)-AMIDE 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: 94.0%

ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (57513-54-9) + 1,2-diamino-benzene (95-54-5) → 4-Hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid (2-amino-phenyl)-amide (151449-78-4)

Guidance literature:

at 150 ℃; for 0.5h;

DOI:10.1007/BF00528643

Reference yield: 65.0%

1,2-diamino-benzene (95-54-5) + 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid methyl ester (84088-50-6) → 4-Hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid (2-amino-phenyl)-amide (151449-78-4)

Guidance literature:

In toluene; at 100 ℃; for 4h;

DOI:10.1021/jm061173n

Reference yield:

N-Methylanthranilic acid (119-68-6) → 4-Hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid (2-amino-phenyl)-amide (151449-78-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-hydroxybenzotriazole; dicyclohexylcarbodiimide / tetrahydrofuran

1.2: NaH / tetrahydrofuran

2.1: 65 percent / toluene / 4 h / 100 °C

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; toluene;

DOI:10.1021/jm061173n

upstream raw materials:

ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

1,2-diamino-benzene

4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid methyl ester

N-Methylanthranilic acid

Refernces

• 1、 Detsi, Anastasia,Bouloumbasi, Dionysia,Prousis, Kyriakos C.,Koufaki, Maria,Athanasellis, Giorgos,Melagraki, Georgia,Afantitis, Antreas,Igglessi-Markopoulou, Olga,Kontogiorgis, Christos,Hadjipavlou-Litina, Dimitra J.. "Design and synthesis of novel quinolinone-3-aminoamides and their α-lipoic acid adducts as antioxidant and anti-inflammatory agents". . p. 2450 - 2458. Retrieved 2008/02/02.