108261-07-0

Basic information

• Product Name: 8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol
• Synonyms: 5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-8-ol;8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol;4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-8-ol
• CAS NO: 108261-07-0
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.25
• Mol File: 108261-07-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol(108261-07-0)
• EPA Substance Registry System: 8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol(108261-07-0)

Safety Data

• Hazardous Substances Data: 108261-07-0(Hazardous Substances Data)

Usage

Description

8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol is an organic compound with a complex chemical structure, characterized by its isoquinolinol backbone and various functional groups, including a methoxy, a methyl, and two methylenedioxy groups. 8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol is known for its potential applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol is used as an intermediate in the synthesis of Cotarnine Chloride (C717500), which is an oxidative degradation product of the drug Noscapine (N882000). 8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol plays a crucial role in the development of new pharmaceuticals, particularly those targeting various medical conditions.
Used in Chemical Synthesis:
In the chemical industry, 8-Methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-4-ol can be utilized as a building block for the synthesis of more complex organic molecules. Its unique structure and functional groups make it a valuable component in the creation of novel compounds with potential applications in various fields, such as materials science, agrochemistry, and more.

Upstream product

• 108261-02-5 -N-methylamino>acetaldehyde dimethyl acetal 
• 108261-01-4 -N-methylamino>acetaldehyde diethyl acetal 
• 50-00-0 formaldehyd 
• 127063-97-2 5,6,7,8-Tetrahydro-4-methoxy-1,3-dioxolo<4,5-g>isoquinolin-8-ol 
• 120-57-0 piperonal 
• 5779-99-7 4-methoxybenzo[d][1,3]dioxole-5-carbaldehyde 
• 137115-13-0 N-(3,4-methylenedioxybenzyl)-N-methyl-2,2-diethoxyethylamine 
• 108261-00-3 amino>acetaldehyde diethyl acetal 
• 108261-05-8 N-(2-methoxy-3,4-methylenedioxybenzyl)-p-toluenesulfonamide 
• 108261-03-6 N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluene-sulfonyl)aminoacetaldehyde diethylacetal 
• 108460-85-1 amino>acetaldehyde dimethyl acetal 
• 128580-99-4 4-Methoxy-5-(2',2'-dimethoxyethyl)carbimino-1,3-benzodioxolan 
• 59259-90-4 5-(dimethoxymethyl)benzo[d][1,3]dioxole 

Downstream Products

• 108434-79-3 5,6,7,8-Tetrahydro-8-acetoxy-4-methoxy-6-methyl-1,3-dioxolo<4,5-g>isoquinoline 
• 550-10-7 hydrocotarnine 
• 82-54-2 4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol 
• 30936-27-7 4-methoxy-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide 
• 108434-83-9 2,3-dihydro-8-methoxy-2-methyl-6,7-methylenedioxy-4(1H)-isoquinolone 
• 128-62-1 (±)-α-noscapine 

Relevant articles and documents

A new total synthesis of (±)-α-noscapine

A new, convergent total synthesis of (±)-α-noscapine was developed on a grams scale through the condensation of 3-trimethylsilyl-meconin derivative 9 and the iodized salt cotarnine derivative 20 as the key step. Staring from simple 2,3-dimethoxybenzoic acid, piperonal and 2,2-dimethoxyethanamine, through the traditional chemical processes to give the final product in 11.6% yield over 14 steps.

Practical Synthesis of 5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxoloisoquinolin-5-ol (Cotarnine)

5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxoloisoquinolin-5-ol (cotarnine, 1), an oxidative degradation product of (3S)-6,7-dimethoxy-3-isoquinolin-5-yl>phthalide (noscapine), has efficiently been synthesized from 2-methoxy-3,4-(methylenedioxy)benzaldehyde (7) in 66percent overall yield. -N-methylamino>acetaldehyde dimethyl acetal, obtained by reductive amination of 7 with aminoacetaldehyde dimethyl acetal followed by N-methylation, was cylized in acid to 5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxoloisoquinolin-8-ol (12).The major byproduct of the cyclization was C-8 methoxy derivative of 12, and the amount of this byproduct was decreased by removal of MeOH formed in the reaction mixture.Acetylation of the hydroxyl group in 12 and hydrogenolysis gave 5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxoloisoquinoline (hydrocotarnine), which was oxidized with I2 followed by basification to afford 1.

Benzylamine derivative

There is provided a novel benzylamine derivative of the formula I: STR1 wherein R1 represents a hydrogen atom or a methyl group, X represents a hydrogen atom, a methyl group or a tosyl group, and Y represents a hydrogen atom, a methyl group or STR2 in which R2 and R3 being identical or different from each other represent independently a lower alkyl group.