30936-27-7

Basic information

• Product Name: 4-METHOXY-6-METHYL-7,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]ISOQUINOLIN-6-IUM, IODIDE
• Synonyms: 4-METHOXY-6-METHYL-7,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]ISOQUINOLIN-6-IUM, IODIDE;7,8-Dihydro-4-Methoxy-6-Methyl-1,3-dioxolo[4,5-g]isoquinoliniuM Iodide
• CAS NO: 30936-27-7
• Molecular Formula: C₁₂H₁₄NO₃*I
• Molecular Weight: 347.14893
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 30936-27-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 184-185 °C
• Appearance: /
• CAS DataBase Reference: 4-METHOXY-6-METHYL-7,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]ISOQUINOLIN-6-IUM, IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-6-METHYL-7,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]ISOQUINOLIN-6-IUM, IODIDE(30936-27-7)
• EPA Substance Registry System: 4-METHOXY-6-METHYL-7,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]ISOQUINOLIN-6-IUM, IODIDE(30936-27-7)

Safety Data

• Hazardous Substances Data: 30936-27-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Crystalline Solid

Upstream product

• 550-10-7 hydrocotarnine 
• 484-30-0 4-Methoxy-1,3-dioxolo<4,5-g>7,8-dihydroisochinolin 
• 74-88-4 methyl iodide 
• 5263-78-5 5,6,7,8-Tetrahydro-4-methoxy-1,3-dioxolo<4,5-g>isoquinoline 
• 5779-99-7 4-methoxybenzo[d][1,3]dioxole-5-carbaldehyde 
• 108261-00-3 amino>acetaldehyde diethyl acetal 
• 108434-79-3 5,6,7,8-Tetrahydro-8-acetoxy-4-methoxy-6-methyl-1,3-dioxolo<4,5-g>isoquinoline 
• 108261-07-0 5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo<4,5-g>isoquinolin-8-ol 
• 108261-01-4 -N-methylamino>acetaldehyde diethyl acetal 
• 108460-85-1 amino>acetaldehyde dimethyl acetal 
• 108261-02-5 -N-methylamino>acetaldehyde dimethyl acetal 
• 128580-99-4 4-Methoxy-5-(2',2'-dimethoxyethyl)carbimino-1,3-benzodioxolan 
• 120-57-0 piperonal 
• 59259-90-4 5-(dimethoxymethyl)benzo[d][1,3]dioxole 

Downstream Products

• 128-62-1 6,7-Dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-isobenzofuran-1-one 
• 85280-20-2 Narcotine 
• 10421-76-8 noscapine 
• 82-54-2 4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol 
• 1005734-51-9 6,7-dimethoxy-2-(4-methoxybenzyl)-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2,3-dihydroisoindol-1-one 
• 128-62-1 (±)-α-noscapine 
• 2220-06-6 2-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-1-phenylethan-1-one 

Relevant articles and documents

Metal-Free Activation of C(sp3)–H Bond, and a Practical and Rapid Synthesis of Privileged 1-Substituted 1,2,3,4-Tetrahydroisoquinolines

The reaction of cotarnine and acyl/aryl ketones in “green” solvents provides an efficient approach to an array of privileged 1,2,3,4-tetrahydroisoquinolines in excellent yields by metal-free activation of C(sp3)–H bonds. This one-pot procedure takes place under base-free conditions at room temperature, and tolerates a wide range of functionalities. The reaction is highly chemoselective, can be performed on a multi-gram scale, and pure products are isolated by simple filtration without workup. Interestingly, the complementary two-step procedure from cotarnine halide salts gives the Mannich products in good yields. The scope was elaborated to 9-bromocotarnine salts to access a range of 9-bromonoscapine-derived analogues. The methodology has been developed considering the structural similarity of cotarnine derivatives to noscapinoids, which represent an emerging class of microtubule-modulating anticancer agents.

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.