80574-72-7

Basic information

• Product Name: N-formyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: N-formyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 80574-72-7
• Molecular Weight: 237.301
• Mol File: 80574-72-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-formyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: N-formyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline(80574-72-7)
• EPA Substance Registry System: N-formyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline(80574-72-7)

Safety Data

• Hazardous Substances Data: 80574-72-7(Hazardous Substances Data)

Upstream product

• 61020-12-0 1-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde 
• 71-43-2 benzene 
• 64-18-6 formic acid 
• 3297-72-1 1-phenylisoquinoline 
• 64-04-0 phenethylamine 
• 23069-99-0 N-(2-phenylethyl)formamide 
• 100-52-7 benzaldehyde 
• 205596-43-6 N-Benzhydryl-N-(2-phenylsulfanyl-ethyl)-formamide 
• 205596-37-8 Benzhydryl-(2-phenylsulfanyl-ethyl)-amine 
• 119-61-9 benzophenone 

Downstream Products

• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 7149-64-6 2-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Gold Particles Supported on Amino-Functionalized Silica Catalyze Transfer Hydrogenation of N-Heterocyclic Compounds

In this work we demonstrate that exceptionally small gold particles (d=0.6±0.2 nm) supported on amino-functionalized mesoporous silicate SBA-15 are highly active in transfer hydrogenation of structurally diverse unsaturated N-heterocyclic compounds. The heterocyclic ring is reduced selectively. The gold particles aggregate to a diameter of 4–5 nm in the presence of formic acid/triethylamine (hydrogen donor) during the first catalytic run. In subsequent cycles the nanoparticles maintain their size, yielding a very stable catalytic system that was recycled more than five times. In contrast, analogous SBA catalysts featuring larger (～5–35 nm) gold particles are not active. Excess formic acid also leads to the formation of formamide derivatives of the products of hydrogenation, which can be deformylated quantitatively. Fifteen structurally different substrates, including the scaffolds of quinoline, isoquinoline, quinoxaline, acridine, phenanthroline, quinazoline, and phenanthridine are hydrogenated and deformylated to give the amine products in >90% overall yield. Deuterium labeling experiments indicate that 1,2-addition with subsequent disproportionation of the formed intermediate is the preferred reaction path over the 1,4-addition one, suggesting the participation of a gold hydride species. (Figure presented.).

A highly efficient synthesis of 1-methyl-, 1-benzyl-, and 1-phenyl-1,2,3,4-tetrahydroisoquinolines by a modified pummerer reaction

(±)-1-Methyl- (13b), (±)-1-benzyl- (13c), and (±)-1-phenyl- (13d)-1,2,3,4-tetrahydroisoquinolines, which are supposed to participate in the pathogenesis of Parkinson's disease, were prepared by using a modified Pummerer reaction as a key step in excellent overall yields from the commercially available ketones (4b-c).

Friedel-Crafts Reactions. IV. The Use of Cyclic N-Formyl-2-Methoxyamines in Electrophilic Amidoalkylation of Aromatic Compounds

Aromatic compounds react with cyclic N-formyl-2-methoxyamines in proton or Lewis acid catalyzed reactions, yielding 2-aryl substituted nitrogen heterocyclic compounds.These products are easily converted to the corresponding N-H and N-CH3 derivatives by acid hydrolysis and LiAlH4 reduction, respectively.