69560-46-9

Basic information

• Product Name: Formamide, N-methyl-N-[1,2,3,4-tetrahydro-6,7-dimethoxy-2-(2,4,5-trimethoxyphenyl )-1-naphthalenyl]-, cis-
• CAS NO: 69560-46-9
• Molecular Formula: C23H29NO6
• Molecular Weight: 415.486
• Mol File: 69560-46-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Formamide, N-methyl-N-[1,2,3,4-tetrahydro-6,7-dimethoxy-2-(2,4,5-trimethoxyphenyl )-1-naphthalenyl]-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: Formamide, N-methyl-N-[1,2,3,4-tetrahydro-6,7-dimethoxy-2-(2,4,5-trimethoxyphenyl )-1-naphthalenyl]-, cis-(69560-46-9)
• EPA Substance Registry System: Formamide, N-methyl-N-[1,2,3,4-tetrahydro-6,7-dimethoxy-2-(2,4,5-trimethoxyphenyl )-1-naphthalenyl]-, cis-(69560-46-9)

Safety Data

• Hazardous Substances Data: 69560-46-9(Hazardous Substances Data)

Upstream product

• 2565-30-2 formyl chloride 
• 69560-44-7 cis-6,7-dimethoxy-N-methyl-2-(2,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-1-naphthylamine 
• 69560-42-5 6,7-dimethoxy-2-(2,4,5-trimethoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one 
• 77287-34-4 formamide 

Downstream Products

• 69560-48-1 6,7-dimethoxy-1-(N-methylformamido)-2-(2,4,5-trimethoxyphenyl)naphthalene 

Relevant articles and documents

Conversion of the Naturally Occurring Amide Alkaloids into O5 Benzophenanthridinium Alkaloids. A New Synthetic Sequence to Antitumour Benzophenanthridine Alkaloids

Cyclisation of methyl integriamide (17a) and methyl isoarnottianamide (17b) by the Bischler-Napieralski reaction gave the naturally occurring O5 benzophenanthridine alkaloids, chelirubine (5a), and chelilutine (5b), respectively; this was extended to give a generally applicable, versatile synthesis of benzophenanthridine alkaloids from 2-aryl-3,4-dihydronaphthalen-1(2H)-ones (13).Treatment of the tetralones (13) with methylamine and titanium tetrachloride followed by sodium borohydride provided the cis-2-aryl-N-methyl-1,2,3,4-tetrahydro-1-naphthylamines (14) which were converted into the N-formyl derivatives (15) with freshly prepared chloral in good yields.Dehydrogenation of the resulting formamides (15) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) gave the fully aromatised amines corresponding to methyl integriamide (17a).Bischler-Napieralski reaction of these amides (17) furnished the desired quaternary benzophenanthridine alkaloids (5).