1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Base Information

• Chemical Name: 1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS No.: 139655-04-2
• Molecular Formula: C17H15N3O2
• Molecular Weight: 293.325
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20392813
• Nikkaji Number: J1.086.319H
• ChEMBL ID: CHEMBL5203765
• Mol file: 139655-04-2.mol

Synonyms:139655-04-2;1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole;1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride;1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-beta-carboline;ChemDiv1_011752;Oprea1_297050;SCHEMBL6780834;CHEMBL5203765;GTZHXBQPFWAUOT-UHFFFAOYSA-;HMS620G04;DTXSID20392813;1H-Pyrido[3,4-b]indole, 2,3,4,9-tetrahydro-1-(4-nitrophenyl)-;STK505570;AKOS000321627;AKOS015964625;AKOS016345723;CS-0357873;EU-0018681;1-(4-Nitrophenyl)-1,2,3,4-tetrahydro-beta-carboline;1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-b-carboline;InChI=1/C17H15N3O2/c21-20(22)12-7-5-11(6-8-12)16-17-14(9-10-18-16)13-3-1-2-4-15(13)19-17/h1-8,16,18-19H,9-10H2

Chemical Property of 1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Chemical Property:

• PSA: 73.64000
• LogP: 4.16320
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 293.116426730
• Heavy Atom Count: 22
• Complexity: 417

Purity/Quality:

98%min ^*data from raw suppliers

1-(4-Nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(C2=C1C3=CC=CC=C3N2)C4=CC=C(C=C4)[N+](=O)[O-]

Technology Process of 1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

There total 17 articles about 1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 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: 100.0%

N-(4-nitrobenzylidene)tryptamine (139655-01-9) → (±)-2,3,4,9-tetrahydro-1-(4-nitrophenyl)-1H-pyrido[3,4-b]indole (139655-04-2)

Guidance literature:

With chloro-trimethyl-silane; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1246/cl.2002.428

Reference yield: 99.0%

tryptamine (61-54-1) + 4-nitrobenzaldehdye (555-16-8) → (±)-2,3,4,9-tetrahydro-1-(4-nitrophenyl)-1H-pyrido[3,4-b]indole (139655-04-2)

Guidance literature:

With 1,1,1,3',3',3'-hexafluoro-propanol; for 1h; Temperature; Solvent; Reflux; Inert atmosphere;

DOI:10.1039/c4ra03628j

Reference yield: 89.0%

tryptamine (61-54-1) + 4-nitrobenzaldehdye (555-16-8) + 4-nitro-benzoic acid (62-23-7) → (±)-2,3,4,9-tetrahydro-1-(4-nitrophenyl)-1H-pyrido[3,4-b]indole (139655-04-2)

Guidance literature:

at 140 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.mcat.2019.02.018

upstream raw materials:

tryptamine

4-nitrobenzaldehdye

chloroformic acid ethyl ester

tryptamine

Downstream raw materials:

1-(4-nitrophenyl)-9H-pyrido[3,4-b]indole

Refernces

• 1、 Han, Feng,Li, Huan,Liu, Haicheng,Liu, Jianping,Xu, Qing. "Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet-Spengler reactions". supporting information. p. 7079 - 7085. Retrieved 2020/10/02.
• 2、 Ramu,Srinath,kumar, A. Aswin,Baskar,Ilango,Balasubramanian. "Metal free one pot synthesis of Β-carbolines via a domino Pictet-Spengler reaction and aromatization". . p. 86 - 93. Retrieved 2019/02/27.