98215-55-5

Upstream product

• 1711-09-7 3-bromobenzoyl chloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 98215-66-8 1-(3-Bromo-phenyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline; hydrochloride 
• 1224508-24-0 6,7-dimethoxy-1-(3-bromophenyl)isoquinoline 
• 67616-16-4 N-[2-(3,4-dimethoxyphenyl)ethyl]benzamide 
• 1448701-59-4 (+)-1-(3-bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 98215-76-0 1-(3-Bromo-phenyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 

Relevant academic research and scientific papers

Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation

A convenient and general asymmetric transfer hydrogenation of a wide array of 1-aryl-3,4-dihydroisoquinoline derivatives using a [RuIICl(η6-benzene)TsDPEN] complex in combination with a 5:2 HCOOH-Et3N azeotropic mixture as a hydrogen source was developed. Under mild reaction conditions, the described catalytic transformation secured a practical synthetic access to the corresponding valuable chiral 1-aryltetrahydroisoquinoline units with high atom economy, a broad substrate scope, high isolated yields (up to 97%) and good to excellent enantioselectivities (up to 99% ee). It was found that the stereochemical outcome of the reaction was strongly influenced by both the structure of the catalyst and the substituents present on the substrate. The synthetic utility of the present protocol has been demonstrated through the asymmetric synthesis of several biologically important alkaloids including the antiepileptic drug agent 1c, as well as (-)-nor-cryptostyline alkaloids I and II.

Dehalogenation of 1-Halogenothienyl-di- and -tetra-hydroisoquinolines by Sodium Methoxide in Dimethyl Sulphoxide

On treatment with sodium methoxide-dimethyl sulphoxide (NaOMe-DMSO) 1-(5-halogeno-2-thienyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolines suffer loss of halogen and are converted into the related 1-hydroxytetrahydroisoquinolines.The reaction fails with comparable 1-bromophenyl- and 1-(halogeno-3-thienyl)tetrahydroisoquinolines.A similar transformation takes place with (5-halogeno-2-thienyl)phenylmethoxymethanes, leading to the dimethyl acetal of the 5-dehalogenated-2-thienyl phenyl ketone. α-Halogenated-2 and 3-thienyl-3,4-dihydroisoquinolines undergo dehalogenation-aromatisation with NaOMe-DMSO.Mechanisms for these conversions are proposed.