70592-30-2

Basic information

• Product Name: Isoquinoline, 6-methoxy-7-(phenylmethoxy)-
• CAS NO: 70592-30-2
• Molecular Formula: C17H15NO2
• Molecular Weight: 265.312
• Mol File: 70592-30-2.mol

Chemical Properties

• CAS DataBase Reference: Isoquinoline, 6-methoxy-7-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 6-methoxy-7-(phenylmethoxy)-(70592-30-2)
• EPA Substance Registry System: Isoquinoline, 6-methoxy-7-(phenylmethoxy)-(70592-30-2)

Safety Data

• Hazardous Substances Data: 70592-30-2(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 22483-09-6 2,2-dimethoxyethylamine 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 133343-21-2 (2R,3R)-2,3-Bis-(3-benzyloxy-4-methoxy-phenyl)-oxirane 
• 150982-70-0 N-(3-Benzyloxy-4-methoxy)-benzylaminoacetaldehyd-dimethylacetal 
• 41462-21-9 N-(3-Benzyloxy-4-methoxy)-benzyliden-aminoacetaldehyd-dimethylacetal 
• 150982-71-1 N-(3-Benzyloxy-4-methoxy)-benzyl-N-tosylaminoacetaldehyd-dimethylacetal 
• 135574-24-2 Benzoic acid (R)-((S)-2-benzoyl-7-benzyloxy-6-methoxy-1,2-dihydro-isoquinolin-1-yl)-(3-benzyloxy-4-methoxy-phenyl)-methyl ester 
• 135574-23-1 (1R,2S)-1,2-Bis-(3-benzyloxy-4-methoxy-phenyl)-2-(2,2-dimethoxy-ethylamino)-ethanol 
• 133343-26-7 (4R,5R)-4,5-Bis-(3-benzyloxy-4-methoxy-phenyl)-[1,3,2]dioxathiolane 2,2-dioxide 
• 133343-22-3 (4R,5R)-4,5-Bis-(3-benzyloxy-4-methoxy-phenyl)-[1,3,2]dioxathiolane 2-oxide 

Downstream Products

• 4594-05-2 7-hydroxy-6-methoxy-1-methylisoquinoline 
• 6835-18-3 7-benzyloxy-6-methoxy-1-methylisoquinoline 

Relevant articles and documents

Aminomethylation/hydrogenolysis as an alternative to direct methylation of metalated isoquinolines - A novel total synthesis of the alkaloid 7-hydroxy-6-methoxy-1-methylisoquinoline

Highly-substituted isoquinolines are important scaffolds in syntheses of natural products and in drug development and hence, effective synthetic approaches are required. Here we present a novel method for the introduction of a methyl group at C1 of isoquinolines. This is exemplified by a new total synthesis of the alkaloid 7-hydroxy-6-methoxy-1-methylisoquinoline. Direct metalation of 7-benzyloxy-6-methoxyisoquinoline with Knochel-Hauser base, followed by cuprate-mediated methylation gives the target alkaloid directly, but separation from the educt is cumbersome. Quenching the metalated intermediate with Eschenmoser's reagent gives an easy to clean tertiary benzylamine, which, after quaternization with iodomethane, is easily converted into the desired 1-methylisoquinoline by hydrogenolysis of both the benzylamine and benzyl ether groups.

Protoberberines from Reissert compounds, II: A new synthesis of 8-methyldibenzo[a,g]quinolizidines

The Reissert compounds 16 are benzylated by 2-bromomethylacetophenone dioxolane 14 to give the dihydroisoquinolines 5. Treatment of 5 with KOH yields the 1-benzylisoquinolines 6 which spontaneously form the deoxygenated coralynes 4 in acidic solution. 4a

Short-cut in the pomeranz-fritsch synthesis of 1-benzyl-isoquinolines; short and efficient syntheses of norrecticuline derivatives and of papaverine

A new methodology for the Pomeranz-Fritsch synthesis of 1-benzyl-1,2-dihydroisoquinolines avoiding pavine or isopavine troubles, has been developed. These intermediates could be reduced to their 1,2,3,4-tetrahydro congeners or aromatized to give isoquinolines, as it was demonstrated by the synthesis of some norrecticuline derivatives 4-7 and of papaverin 8.