109802-64-4

Basic information

• Product Name: ETHYL 3-PHENYL-4-ISOQUINOLINECARBOXYLATE
• Synonyms: ETHYL 3-PHENYL-4-ISOQUINOLINECARBOXYLATE
• CAS NO: 109802-64-4
• Molecular Formula: C₁₈H₁₅NO₂
• Molecular Weight: 277.32
• Mol File: 109802-64-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL 3-PHENYL-4-ISOQUINOLINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-PHENYL-4-ISOQUINOLINECARBOXYLATE(109802-64-4)
• EPA Substance Registry System: ETHYL 3-PHENYL-4-ISOQUINOLINECARBOXYLATE(109802-64-4)

Safety Data

• Hazardous Substances Data: 109802-64-4(Hazardous Substances Data)

Upstream product

• 2216-94-6 phenylpropynoic acid ethyl ester 
• 26260-02-6 2-iodobenzaldehyde 
• 212505-57-2 N-(2-iodobenzylidene)-2-methylpropan-2-amine 
• 109802-44-0 {Pd(C(Ph)=C(CO2Et)C6H4CH2NMe2(cyclic))(μ-I)}2 

Downstream Products

• 1401424-87-0 ethyl 3-phenyl-1,2,3,4-tetrahydroisoquinoline-4-carboxylate 

Relevant articles and documents

Synthesis of Isoquinolines and Pyridines via Palladium-Catalyzed Iminoannulation of Internal Acetylenes

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Assembly of isoquinolines via CuI-catalyzed coupling of β-keto esters and 2-halobenzylamines

(Chemical Equation Presented) CuI-catalyzed coupling of 2-halobenzylamines with β-keto esters or 1,3-diketones in i-PrOH under the action of K 2CO3 produced 1,2-dihydroisoquinolines as the coupling/condensative cyclization products,

Synthesis of isoquinolines and pyridines by the palladium-catalyzed iminoannulation of internal alkynes

A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)2, an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.