55755-16-3

Usage

Chemical Properties

clear colorless liquid

Uses

It is employed as intermediate for pharmaceutical and organic synthesis

InChI:InChI=1/C9H13N/c1-8-4-2-3-5-9(8)6-7-10/h2-5H,6-7,10H2,1H3

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 64-17-5 ethanol 
• 22364-68-7 2-tolylmethylnitrile 
• 28638-59-7 methyl-2 β-nitrostyrene 
• 103028-79-1 3-o-tolyl-propionic acid amide 

Downstream Products

• 857822-30-1 2-(2-methylphenyl)ethylformamide 
• 736054-86-7 C₂₂H₂₈N₂O₃ 
• 756500-61-5 N-methyl-2-(o-tolyl)ethan-1-amine 
• 947304-09-8 C₃₀H₄₃N₃O₃ 
• 947303-96-0 C₁₈H₂₈N₂O₂ 
• 736054-82-3 3-aminomethyl-N-(2-o-tolyl-ethyl)-benzamide 

Relevant academic research and scientific papers

Direct Access to Primary Amines from Alkenes by Selective Metal-Free Hydroamination

Direct and selective synthesis of primary amines from easily available precursors is attractive yet challenging. Herein, we report the rapid synthesis of primary amines from alkenes via metal-free regioselective hydroamination at room temperature. Ammonium carbonate was used as ammonia surrogate for the first time, allowing for efficient conversion of terminal and internal alkenes into linear, α-branched, and α-tertiary primary amines under mild conditions. This method provides a straightforward and powerful approach to a wide spectrum of advanced, highly functionalized primary amines which are of particular interest in pharmaceutical chemistry and other areas.

METHOD OF HYDROBORATING ALCOHOLS AND REDUCING FUNCTIONAL GROUPS USING A RECYCLABLE FLUOROUS BORANE-SULFIDE

A method of hydroborating an alkene or alkyne, or reducing an organic functionality, oxidizing primary and secondary alcohols using a fluorous borane-sulfide is disclosed. The method includes regeneration and recycling the fluorous borane-sulfide.

Fluorous dimethyl sulfide: A convenient, odorless, recyclable borane carrier

(matrix presented) Borane gas and 2-(perfluorooctyl)ethyl methyl sulfide form a solid comprised of an approximately 1:1 mixture (fluorous BMS) of sulfide and the corresponding sulfide-borane. Fluorous BMS permits hydroboration of alkenes in a dichloromethane/perfluorinated hydrocarbon mixture with subsequent recycling of the fluorous sulfide by fluorous extraction. The use of fluorous BMS in the asymmetric reduction of ketones catalyzed by a chiral oxaborolidine catalyst, and in the reduction of other functional groups, is also reported.

Synthesis and Antitumor Activity of 4- and 5-Substituted Derivatives of Isoquinoline-1-carboxaldehyde Thiosemicarbazone

Various substituted isoquinoline-1-carboxaldehyde thiosemicarbazones (12 compounds) have been synthesized and evaluated for antineoplastic activity in mice bearing the L1210 leukemia.Condensation of 4-bromo-1-methylisoquinoline (4) with ammonium hydroxide, methylamine, ethylamine, and N-acetylethylenediamine gave the corresponding 4-amino, 4-methylamino, 4-ethylamino, and 4-N-(acetylethyl)amino derivatives, which were then converted to amides and subsequently oxidized to aldehydes followed by condensation with thiosemicarbazide to yield thiosemicarbazones 8a-c, 9a-c, and 16.Nitration of 4, followed by oxidation with selenium dioxide, produced aldehyde 18, which was then converted to the cyclic ethylene acetal 19.Condensation of 19 with morpholine followed by catalytic reduction of the nitro group and treatment with thiosemicarbazide afforded 5-amino-4-morpholinoisoquinoline-1-carboxaldehyde thiosemicarbazone (22).N-Oxidation of 1,5-dimethylisoquinoline, followed by rearrangement with acetic anhydride, gave, after acid hydrolysis, 1,5-dimethyl-4-hydroxyisoquinoline, which was converted to its acetate and then oxidized to yield 4-acetoxy-5-methylisoquinoline-1-carboxaldehyde (32).Sulfonation of 1,4-dimethylisoquinoline, followed by reaction with potassium hydroxide, acetylation, and oxidation, gave 5-acetoxy-4-methylisoquinoline-1-carboxaldehyde (40).Condensation of compounds 32 and 39 with thiosemicarbazide afforded the respective 4- and 5-acetoxy(5- and 4-methyl)thiosemicarbazones 33 and 40, which were then converted to their respective 4- and 5-hydroxy derivatives 34 and 41 by acid hydrolysis.The most active compounds synthesized were 4-aminoisoquinoline-1-carboxaldehyde thiosemicarbazone (9a) and 4- (methylamino)isoquinoline-1-carboxaldehyde thiosemicarbazone (9b), which both produced optimum percent T/C values of 177 against the L1210 leukemia in mice when used at daily dosage of 40 mg/kg for 6 consecutive days.Furthermore, when 9a was given twice daily at a dosage of 40 mg/kg for 6 consecutive days, a T/C value of 165 was obtained and 60percent of the mice were 60-day long-term survivors.

Process for the preparation of (8As,12AS,13AS)-decahydroisoquino ((2,1-G) (1,6)-naphthyridin-8-one derivatives

The invention provides a process for preparing single enantiomers of compounds represented by the formula: STR1 and chiral acid addition salts thereof; wherein: X and Y are independently hydrogen; lower alkyl; lower alkoxy; or halo; or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy; which includes reduction of a compound represented by the formula: STR2 to give a mixture of stereoisomers represented by the formula: STR3 wherein each wavy line independently represents a bond in either the α or β position; followed by dissolving the mixture of stereoisomers and a chiral resolving acid in a suitable solvent and allowing the solution to crystallize, giving a salt of the desired enantiomer.

Substituted 1-(aminomethyl)-2-(arylacetyl)-1,2,3,4- tetrahydroisoquinolines: A novel class of very potent antinociceptive agents with varying degrees of selectivity for κ and μ opioid receptors

This study describes the synthesis of a series of novel substituted 1- (aminomethyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinolines, and discusses their structure-activity relationships (SARs) using binding affinity for opioid receptors and antinociceptive potency as the indices of biological activity. The introduction of a hydroxy substituent in position 5 of the isoquinoline nucleus generated a compound, 40, which is 2 times more potent than the previously disclosed unsubstituted analogue 39 in mouse models of antinociception. A QSAR analysis of the 5-substitution clearly demonstrates that antinociceptive activity is inversely associated with the lipophilicity of the substituents. The substituted compounds described herein are less selective for the κ opioid receptors than the unsubstituted isoquinoline 39. For example, the 5-hydroxy-substituted compound 59 shows high affinity for κ opioid receptors (K(i) κ = 0.09 nM) and a (K(i) μ/K(i) κ ratio of only 5. However, a multiple linear regression analysis demonstrates a lack of correlation between antinociceptive activity and affinity for the μ opioid receptor. On the other hand, the correlation between binding affinity to κ opioid receptor and antinociceptive activity was statistically significant.

PHOTOREACTION OF PHTHALIMIDES POSSESSING AN ORTHO-METHYLPHENYL GROUP IN THEIR N-SIDE CHAIN. SYNTHESIS OF TETRACYCLIC NITROGEN HETEROCYCLES

Upon irradiation phthalimides (5 and 8) possesing o-methylphenyl group in their N-side chain gave mainly the tetracyclic ring systems (9 and 10).It was shown that the photocyclization occurs at ε- or ζ-position across the carbons of the benzene ring (B-ring).