95688-78-1

Basic information

• Product Name: Formamide, N-methyl-N-[5,6,7,8-tetrahydro-6-(2,4,5-trimethoxyphenyl)naphtho[2,3-d ]-1,3-dioxol-5-yl]-, cis-
• CAS NO: 95688-78-1
• Molecular Formula: C22H25NO6
• Molecular Weight: 399.444
• Mol File: 95688-78-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Formamide, N-methyl-N-[5,6,7,8-tetrahydro-6-(2,4,5-trimethoxyphenyl)naphtho[2,3-d ]-1,3-dioxol-5-yl]-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: Formamide, N-methyl-N-[5,6,7,8-tetrahydro-6-(2,4,5-trimethoxyphenyl)naphtho[2,3-d ]-1,3-dioxol-5-yl]-, cis-(95688-78-1)
• EPA Substance Registry System: Formamide, N-methyl-N-[5,6,7,8-tetrahydro-6-(2,4,5-trimethoxyphenyl)naphtho[2,3-d ]-1,3-dioxol-5-yl]-, cis-(95688-78-1)

Safety Data

• Hazardous Substances Data: 95688-78-1(Hazardous Substances Data)

Upstream product

• 88775-70-6 6,7-methylenedioxy-2-(2,4,5-trimethoxyphenyl)-3,4-dihydronaphthalen-1(2H)-one 
• 2565-30-2 formyl chloride 
• 95689-09-1 cis-N-methyl-6,7-methylenedioxy-2-(2,4,5-trimethoxy)-1,2,3,4-tetrahydro-1-naphthylamine 

Downstream Products

• 66216-58-8 6,7-methylenedioxy-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).