30696-07-2

Basic information

• Product Name: N-Phenylquinoline-4-amine
• Synonyms: 4-Anilinoquinoline;N-Phenylquinoline-4-amine;n-phenylquinolin-4-aMine
• CAS NO: 30696-07-2
• Molecular Formula: C₁₅H₁₂N₂
• Molecular Weight: 220.28
• Mol File: 30696-07-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 230 °C
• Boiling Point: 380.2±17.0 °C(Predicted)
• Appearance: /
• Density: 1.204±0.06 g/cm3(Predicted)
• PKA: 6.70±0.13(Predicted)
• CAS DataBase Reference: N-Phenylquinoline-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenylquinoline-4-amine(30696-07-2)
• EPA Substance Registry System: N-Phenylquinoline-4-amine(30696-07-2)

Safety Data

• Hazardous Substances Data: 30696-07-2(Hazardous Substances Data)

Usage

Synthesis

N-phenylquinolin-4-amine was prepared by adding aniline to 4-chloroquinoline ethanol solution under microwave irradiation at 165°C.Experiment steps：To a solution of 4-chloroquinoline (350 mg, 2.14 mmol) in ethanol (3 ml), aniline (996 mg, 10.7 mmol) was added and the mixture was reacted at 165 °C for 3 hours under microwave radiation. The reaction mixture was concentrated in vacuo, aqueous sodium carbonate (25 ml) was added and this was then extracted using dichloromethane (3×30 ml). The organic extracts were collected, dried using magnesium sulphate, concentrated in vacuo and the resulting residue was purified by flash column chromatography eluting with 2% methanol in dichloromethane to give N-phenylquinolin-4-amine as a colourless solid (42 mg, 9%).

Upstream product

• 1035458-54-8 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)quinoline 
• 62-53-3 aniline 
• 142-04-1 aniline hydrochloride 
• 65148-06-3 N-((4-methylphenyl)sulfonyl)-N-phenyl-beta-alanine 
• 6628-93-9 4-anilino-quinolin-2-ol 
• 205985-49-5 4-chloro-3-quinolinesulfonic acid 
• 157494-40-1 4-chloro-3-quinolinesulfonyl chloride 
• 611-36-9 quinolin-4-ol 
• 3964-04-3 4-bromoquinoline 
• 529-37-3 4(1H)-quinolinone 
• 103-71-9 phenyl isocyanate 
• 50634-27-0 1,4-dithiino[2,3-c:5,6-c']diquinoline 
• 824935-59-3 4-anilino-2-chloroquinoline 
• 611-35-8 4-chloroquinoline 

Downstream Products

• 681828-44-4 N-phenyl-N-1,2,3,4-tetrahydroquinolin-4-ylacetamide 
• 681828-43-3 cis-N-Phenyl-N-[1-(thiophene-2-carbonyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide 
• 681828-29-5 N-phenyl-N-quinolin-4-yl-acetamide 

Relevant articles and documents

Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity

We report an investigation of the Chan-Lam amination reaction. A combination of spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description to be presented, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing and unsolved amine and organoboron limitations of this valuable transformation.

Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists

Quinoline, isoquinoline, quinoxaline, and quinazoline derivatives were synthesized using microwave-assisted synthesis and their CB1/CB2 receptor activities were determined using the [35S]GTPγS binding assay. Most of the prepared quinoline, isoquinoline, and quinoxalinyl phenyl amines showed low-potency partial CB2 receptor agonists activity. The most potent CB2 ligand was the 4-morpholinylmethanone derivative (compound 40e) (-log EC 50 = 7.8; Emax = 75%). The isoquinolin-1-yl(3- trifluoromethyl-phenyl)amine (compound 26c) was a high efficacy CB2 agonist (-log EC50 = 5.8; Emax = 128%). No significant CB1 receptor activation or inactivation was shown in these studies, except 40e, which showed weak CB1 agonist activity (CB1 -log EC50 = 5.0). These ligands serve as novel templates for the development of selective CB2 receptor agonist.

Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives

A three-step synthesis of indoloquinoline alkaloids is described. The reaction of 2,3 and 4-substituted haloquinolines with anilines afforded the respective anilinoquinolines, which upon photocyclization gave the indoloquinolines. By regioselective methylation on quinoline nitrogen, furnished the alkaloids cryptotackieine, cryptosanguinolentine, cryptolepine, and the synthetic isomer isoneocryptolepine. Their methyl derivatives were also synthesized in search of new antiplasmodial drugs and DNA intercalating agents.