1125-80-0

Basic information

• Product Name: 3-METHYLISOQUINOLINE
• Synonyms: 3-methyl-isoquinolin;3-METHYLISOQUINOLINE;ISOQUINOLINE, 3-METHYL-;3-(Bromomethyl)isoquinoline
• CAS NO: 1125-80-0
• Molecular Formula: C₁₀H₉N
• Molecular Weight: 143.19
• EINECS: 214-412-5
• Product Categories: Isoquinoline Derivertives;Building Blocks;Heterocyclic Building Blocks;Isoquinolines
• Mol File: 1125-80-0.mol

Chemical Properties

• Melting Point: 63-65 °C(lit.)
• Boiling Point: 251 °C(lit.)
• Flash Point: 106.7 °C
• Appearance: /
• Density: 1.0584 (estimate)
• Vapor Pressure: 0.0436mmHg at 25°C
• Refractive Index: 1.6152 (estimate)
• PKA: 5.66±0.30(Predicted)
• Water Solubility: 919mg/L(20 oC)
• CAS DataBase Reference: 3-METHYLISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLISOQUINOLINE(1125-80-0)
• EPA Substance Registry System: 3-METHYLISOQUINOLINE(1125-80-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: NX2000000
• Hazardous Substances Data: 1125-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYLISOQUINOLINE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its application reason is due to its unique chemical structure, which can be further modified to create a range of bioactive molecules with potential therapeutic properties.
Used in Chemical Synthesis:
3-METHYLISOQUINOLINE is used as a starting material for the preparation of other organic compounds, such as 3-aminoisoquinoline. The application reason is its reactivity and the ability to undergo various chemical reactions, making it a versatile building block in organic synthesis.
In the provided materials, the metabolites of 3-METHYLISOQUINOLINE were separated by adsorption and reversed-phase high-performance liquid chromatography (HPLC), which demonstrates its use in analytical chemistry for the identification and purification of related compounds.

Preparation

Benzylamine (9.18 mL, 84.0 mmol) and 1,1-dimethoxypropan-2-one (9.95 mL, 84.0 mmol) were added to dichloromethane (350 mL) at room temperature. Sodium triacetoxyborohydride (25 g, 118 mmol) was added to the reaction mixture in one portion. The reaction was stirred at room temperature overnight. The reaction mixture was then diluted with 2.5% sodium bicarbonate (250 mL) and mixed for 30 minutes, becoming biphasic. The organic layer was discarded. The aqueous layer was basified to pH 14 using concentrated sodium hydroxide. The basified aqueous solution was washed three times with ethyl acetate and the organic layers were kept and combined. Then, the resulting solution was washed with 5% sodium chloride solution three times. The organic layers were combined and dried over sodium sulfate. The resulting solution was evaporated to a yellow oil, which was found to be N-benzyl-1,1-dimethoxypropan-2-one. The oil (2.62 g, 12.5 mmol) was added dropwise to chlorosulfonic acid (8.35 mL, 125 mmol) over ice. A few milliliters of dichloromethane was used to rinse the oil from its reaction flask and the oil dissolved in dichloromethane was also added to the chlorosulfonic acid flask over ice. The reaction mixture was placed over boiling water for 5 minutes with a condenser to evaporate the solvent used to rinse the N-benzyl-1,1-dimethoxypropan-2-one out of its previous flask while not letting any water vapor enter the flask before the reaction mixture was fully heated. Then, the reaction mixture was placed in the boiling water for 10 minutes without a condenser to allow methanol, a side-product of the reaction, to evaporate out of the flask and drive the reaction forward. After cooling, the reaction mixture was quenched with ice and then basified to pH 14 with concentrated sodium hydroxide. The mixture was washed with dichloromethane three times. The organic layers were combined and dried using magnesium sulfate. The resulting solution was evaporated to solid 3-methylisoquinoline (average percent yield: 2-5%) and the structure was confirmed with GC-MS and NMR.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 3959, 1985 DOI: 10.1016/S0040-4039(00)98697-0Chemical and Pharmaceutical Bulletin, 35, p. 4964, 1987 DOI: 10.1248/cpb.35.4964

InChI:InChI=1/C10H9N/c1-8-6-9-4-2-3-5-10(9)7-11-8/h2-7H,1H3

Upstream product

• 14123-78-5 3-methyl-3,4-dihydro-isoquinoline 
• 63830-81-9 2-(2-oxopropyl)benzaldehyde 
• 109950-11-0 N-Benzyl-N-(2,2-dimethoxy-1-methyl-ethyl)-4-methyl-benzenesulfonamide 
• 67-64-1 acetone 
• 89-97-4 2-CHLOROBENZYLAMINE 
• 10034-85-2 hydrogen iodide 
• 7115-16-4 1-chloro-3-methyl-isoquinoline 
• 7114-80-9 3-methylisoquinolin-1-ol 
• 5423-95-0 3-methyl-isoquinoline-1,4-diol 
• 22148-75-0 (+/-)-N-(1-methyl-2-phenylethyl)formamide 
• 6852-58-0 N-benzylidene tert-butylamine 
• 54879-85-5 2-(2-methylbenzylamino)acetaldehyde dimethyl acetal 
• 541-41-3 chloroformic acid ethyl ester 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 64047-59-2 3-methyl-2-(3-trimethylammonio-propyl)-isoquinolinium; dibromide 
• 104293-83-6 2-propyl-benzylamine 
• 19079-90-4 trans-3-styrylisoquinoline 
• 21259-77-8 2-benzoyl-3-methyl-1,2-dihydroisoquinoline-1-carbonitrile 
• 6275-38-3 3,3'-dimethyl-2,2'-decanediyl-bis-isoquinolinium; dibromide 
• 6277-82-3 3-methyl-2-phenethyl-isoquinolinium; bromide 
• 7114-78-5 2,3-Dimethyl-1-oxo-1,2-dihydroisoquinoline 
• 450-53-3 2-(4-fluoro-phenacyl)-3-methyl-isoquinolinium; bromide 
• 6276-47-7 2-(4-methoxy-phenacyl)-3-methyl-isoquinolinium; iodide 
• 108981-24-4 3-phenethyl-isoquinoline 
• 113058-41-6 3-(1-benzyl-2-phenyl-ethyl)-isoquinoline 
• 32431-36-0 2,3-dimethylisoquinolinium iodide 
• 5470-80-4 3-formylisoquinoline 
• 54804-44-3 3-(Bromomethyl)isoquinoline 

Relevant articles and documents

Synthesis of Isoquinolines from Indenes

A general procedure for the synthesis of isoquinolines from appropriately substituted indenes is described.Ozonolysis of the indenes followed by reductive workup gives intermediate homophthalaldehydes which are treated with ammonium hydroxide to give the isoquinolines.This "one-pot", three-step reaction sequence was applied to the formation of all of the mono-C-methyl-substituted isoquinolines in a regiospecific manner.The procedure is applicable to both electron-withdrawing and electron-donating substituents on the indene system.In this manner the 6- and 7-nitro-,-bromo-, and -iodoisoquinolines were prepared.

Palladium-Catalyzed Isoquinoline Synthesis by Tandem C-H Allylation and Oxidative Cyclization of Benzylamines with Allyl Acetate

A novel approach to synthesize 3-methylisoquinolines via a one-pot, two-step, palladium(II)-catalyzed tandem C-H allylation/intermolecular amination and aromatization is reported. A wide series of 3-methylisoquinoline derivatives were obtained directly using this method in moderate to good yields, and we highlight the synthetic importance of this new transformation.

Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands

An efficient and straightforward method was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods can directly afford the corresponding axially chiral heterobiaryls.

Preparation method of isoquinoline compound

The invention discloses a preparation method of isoquinoline compounds, benzylamine protected by oxamide and allyl acetate are used as raw materials, a series of isoquinoline compounds are obtained through a cascade reaction of C-H bond functionalization and hydrolysis and two-step one-pot synthesis, and the used raw materials are simple and easy to obtain, reaction conditions are mild, and post-treatment is simple.

Potassium tert-Butoxide-Promoted Acceptorless Dehydrogenation of N-Heterocycles

Potassium tert-butoxide-promoted acceptorless dehydrogenation of N-heterocycles was efficiently realized for the generation of N-heteroarenes and hydrogen gas under transition-metal-free conditions. In the presence of KOtBu base, a variety of six- and five-membered N-heterocyclic compounds efficiently underwent acceptorless dehydrogenation to afford the corresponding N-heteroarenes and H2 gas in o-xylene at 140 °C. The present protocol provides a convenient route to aromatic nitrogen-containing compounds and H2 gas. (Figure presented.).

Synthesis of Arylamines via Non-Aerobic Dehydrogenation Using a Palladium/Carbon-Ethylene System

The reaction of cyclohexanones with amines proceeded under an ethylene atmosphere in the presence of a catalytic amount of palladium/carbon to afford a variety of arylamines in good to high yields. The present reaction was carried out under completely non-aerobic conditions, and which is in contrast with the previously reported aerobic system. has wide applicability affording a variety of aromatic amines, and co-product of the reaction is only gaseous ethane. Thus, this method is environmentally friendly. This protocol was applied intramolecularly to provide a novel method for the construction of quinoline and isoquinoline compounds. (Figure presented.).

Asymmetric synthesis of a TRPV1 antagonist via tert -butanesulfinamide- directed reductive amination with a chromanone

An expedient asymmetric synthesis of TRPV1 antagonist 1 has been developed and demonstrated on multikilogram scale. The enabling route to 1 is detailed herein and characterized by the following key transformations: an aldol-cyclodehydration sequence to install the chromanone, and an auxiliary-mediated diastereoselective reductive amination.

New reactions of N-tert-butylimines; Formation of N-heterocycles by methyl radical elimination on flash vacuum thermolysis of N-benzylidene- and N-(2-pyridylmethylidene)-tert-butylamines

Thermal reactions of N-benzylidene- and N-(2-pyridylmethylidene)-tert- butylamines (5 and 13) under FVT conditions have been investigated. Unexpectedly, at 800 °C, compound 5 yields 1,2-dimethylindole and 3-methylisoquinoline. In the reaction of 13 at 800 °C, 3-methylimidazo[1,5- a]pyridine was obtained as the major product. Mechanisms of these reactions have been proposed on the basis of DFT calculations. Furthermore, UV-photoelectron spectroscopy combined with FVT has been applied for direct monitoring and characterization of the thermolysis products in situ. Copyright

Acceptorless dehydrogenation of nitrogen heterocycles with a versatile iridium catalyst

Gas up: A cyclometalated iridium complex is found to catalyze the dehydrogenation of various benzofused N-heterocycles, thus releasing H 2. Driven by as low as 0.1 mol % catalyst, the reaction affords quinolines, indoles, quinoxalines, isoquinolines, and β-carbolines in high yields. Copyright

Synthesis of 6-methyl-8H-dibenzo[a,g]quinolizin-8-imines via Reissert compounds

Alkylation of Reissert compounds derived from 3-methylisoquinolines with several 2-cyanobenzylbromides followed by hydrolytic cleavage provided the corresponding 1-benzyl-3-methylisoquinolines. Treatment of the latter with methylmagnesiumiodide caused cyclization to the title compounds rather than formation of 2-acetylbenzylisoquinolines.