53654-28-7

Upstream product

• 28971-03-1 4-methyl-5,6,7,8-tetrahydroquinoline 
• 30182-67-3 1,3-Cyclohexanedione 
• 5220-49-5 3-amino-cyclohex-2-enone 
• 123-73-9 crotonaldehyde 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 

Downstream Products

• 101068-69-3 4-Methyl-5-benzyl-5,6,7,8-tetrahydrochinolin 
• 101068-70-6 4-Methyl-5-(3-methoxybenzyl)-5,6,7,8-tetrahydrochinolin 
• 101068-72-8 4-Methyl-5-(4-methoxybenzyl)-5,6,7,8-tetrahydrochinolin 
• 101068-71-7 4-Methyl-5-(2-methoxybenzyl)-5,6,7,8-tetrahydrochinolin 
• 115177-36-1 4-Methyl-5-(3,4-dimethoxybenzyl)-5,6,7,8-tetrahydrochinolin 

Relevant academic research and scientific papers

A simple, efficient method for regioselective synthesis of 7-aminomethyl-7,8-dihydro-6H-quinolin-5-ones, new potential CNS agents

We have developed an efficient and convenient strategy for the regioselective synthesis of new conformationally restricted butyrophenones of the quinoline series. The 7-aminomethyl-7,8-dihydro-6H-quinolin-5-ones 9 were obtained from protected alcohol 5 via the tosylate, and also in a one-pot reaction via bromo derivative 6, with moderate-to-good overall yields in both cases. (C) 2000 Elsevier Science Ltd.

A regioselective synthesis of 4-methyl-1-pyrindan-5-one

The enamine 7 reacts with crotonic aldehyde in the presence of p-toluenesulphonic acid via the intermediate 8 to yield regioselectively the unknown title compound 9. In alkaline medium, 9 is also formed from 7 and acetylacetaldehyde dimethyl acetal as well as small amounts of 11 and 12; under acidic conditions, however, mixtures of the regioisomers 9/9a are obtained in poor yield. 9a can be separated by fractional crystallisation of the hydrochlorides. Corresponding to 7 the homologous enamine 13 and acetylacetaldehyde acetal by alkaline catalysis gives the 4-methyltetrahydroquinolinone 1, respectively. Improved experimental details for an efficient preparation of the starting compounds 3 and 4 are given.