N-(2-methylbenzoyl)-8-aminoquinoline

Base Information

• Chemical Name: N-(2-methylbenzoyl)-8-aminoquinoline
• CAS No.: 1182669-71-1
• Molecular Formula: C₁₇H₁₄N₂O
• Molecular Weight: 262.311
• Mol file: 1182669-71-1.mol

Synonyms:N-(2-methylbenzoyl)-8-aminoquinoline

Chemical Property of N-(2-methylbenzoyl)-8-aminoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2-methylbenzoyl)-8-aminoquinoline

There total 19 articles about N-(2-methylbenzoyl)-8-aminoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

8-amino quinoline (578-66-5) + ortho-toluoyl chloride (933-88-0) → N-(2-methylbenzoyl)-8-aminoquinoline (1182669-71-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield: 93.0%

ortho-methylbenzoic acid (118-90-1) + 8-amino quinoline (578-66-5) → N-(2-methylbenzoyl)-8-aminoquinoline (1182669-71-1)

Guidance literature:

ortho-methylbenzoic acid; With thionyl chloride; Inert atmosphere;

8-amino quinoline; With triethylamine; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.3184/174751913X13801883437178

Reference yield: 91.0%

N-quinolin-8-yl-benzamide (33757-48-1) + trimethylaluminum (75-24-1) → N-(2-methylbenzoyl)-8-aminoquinoline (1182669-71-1)

Guidance literature:

With cobalt(III) acetylacetonate; 2,3-DCB; triphenylphosphine; In tetrahydrofuran; toluene; at 80 ℃; for 20h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02860

upstream raw materials:

8-amino quinoline

ortho-toluoyl chloride

ortho-methylbenzoic acid

N-quinolin-8-yl-benzamide

Downstream raw materials:

3-methyl-2-(quinolin-8-ylcarbamoyl)phenyl acetate

6-methyl-N-(quinolin-8-yl)-2-((triisopropylsilyl)ethynyl)-benzamide

2-[⁽²⁾H₃]-methyl-N-(8-quinolinyl)-6-((triisopropylsilyl)ethynyl)-[⁽²⁾H₄]-benzamide

2-allyl-6-methyl-N-(quinolin-8-yl)benzamide

Refernces

• 1、 Khan, Bhuttu,Khan, Afsar Ali,Kant, Ruchir,Koley, Dipankar. "Directing Group-Assisted Copper(II)-Catalyzed ortho-Carbonylation to Benzamide using 2,2′-Azobisisobutyronitrile (AIBN)". . p. 3753 - 3758. Retrieved 2016.
• 2、 Zhan, Fuxu,Zhang, Wei,Zhao, Huaiqing. "Copper/Silver Cocatalyzed Regioselective C5-H Functionalization of 8-Aminoquinoline Amides with 1,3-Dicarbonyl Compounds". . p. 1007 - 1014. Retrieved 2020.
• 3、 Zhu, Longzhi,Sheng, Xinghao,Li, You,Lu, Dong,Qiu, Renhua,Kambe, Nobuaki. "Nickel-Catalyzed Remote C4-H Arylation of 8-Aminoquinolines". . p. 6785 - 6789. Retrieved 2019.
• 4、 Zhou, Yunfei,Zhu, Jianming,Li, Bo,Zhang, Yong,Feng, Jia,Hall, Adrian,Shi, Jiye,Zhu, Weiliang. "Access to different isomeric dibenzoxazepinones through copper-catalyzed C-H etherification and C-N bond construction with controllable smiles rearrangement". . p. 380 - 383. Retrieved 2016.
• 5、 Shang, Rui,Ilies, Laurean,Asako, Sobi,Nakamura, Eiichi. "Iron-catalyzed C(sp2)-H bond functionalization with organoboron compounds". . p. 14349 - 14352. Retrieved 2014.
• 6、 Yi, Hong,Chen, Hong,Bian, Changliang,Tang, Zilu,Singh, Atul K.,Qi, Xiaotian,Yue, Xiaoyu,Lan, Yu,Lee, Jyh-Fu,Lei, Aiwen. "Coordination strategy-induced selective C-H amination of 8-aminoquinolines". . p. 6736 - 6739. Retrieved 2017.
• 7、 Grigorjeva, Liene,Daugulis, Olafs. "Cobalt-promoted dimerization of aminoquinoline benzamides". . p. 1204 - 1207. Retrieved 2015.
• 8、 Lin, Xinxin,Zeng, Cuilian,Liu, Chengkou,Fang, Zheng,Guo, Kai. "C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane". supporting information. p. 1352 - 1357. Retrieved 2021/02/26.
• 9、 Sunnam, Sunil Kumar,Belani, Jitendra D.. "Aryne Multicomponent Reactions by Directed C?H Activation". supporting information. p. 8846 - 8850. Retrieved 2021/05/31.