Nornitidine

Base Information

• Chemical Name: Nornitidine
• CAS No.: 18034-03-2
• Molecular Formula: C₂₀H₁₅NO₄
• Molecular Weight: 333.343
• NSC Number: 166719
• DSSTox Substance ID: DTXSID60304657
• Nikkaji Number: J743.712I
• Wikidata: Q82050742
• Metabolomics Workbench ID: 142004
• ChEMBL ID: CHEMBL521226
• Mol file: 18034-03-2.mol

Synonyms:NSC166719;18034-03-2;CHEMBL521226;SCHEMBL11742867;DTXSID60304657;NSC-166719

Chemical Property of Nornitidine

Chemical Property:

• Vapor Pressure: 9.27E-12mmHg at 25°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 333.10010796
• Heavy Atom Count: 25
• Complexity: 488

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C3=C(C4=CC5=C(C=C4C=C3)OCO5)N=CC2=C1)OC

Technology Process of Nornitidine

There total 86 articles about Nornitidine 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: 99.0%

N-[6-(3,4-Dimethoxy-phenyl)-naphtho[2,3-d][1,3]dioxol-5-yl]-formamide (180411-21-6) → nornitidine (18034-03-2)

Guidance literature:

With trichlorophosphate; In acetonitrile; for 0.833333h;

DOI:10.1039/p19960001647

Reference yield: 97.0%

11,12-dihydro-8,9-dimethoxy-2,3-methylenedioxybenzo[c]phenanthridine (54022-61-6) → nornitidine (18034-03-2)

Guidance literature:

With 10% Pd on charcoal; In 1,2-dichloro-benzene; at 180 ℃;

DOI:10.1016/j.tetlet.2008.11.076

Reference yield: 96.0%

(E)-4,5-dimethoxy-2-(naphtho[2,3-d][1,3]dioxol-6-yl)benzaldehyde O-4-(trifluoromethyl)benzoyl oxime → nornitidine (18034-03-2)

Guidance literature:

With fac-tris(2-phenylpyridinato-N,C₂')iridium(III); In N,N-dimethyl-formamide; at 26 ℃; Inert atmosphere; Irradiation;

DOI:10.1002/anie.201411342

upstream raw materials:

8,9-dimethoxy-6-methyl-2,3-methylenedioxybenzophenanthridine

2,3-dimethoxy-4b,5,6,11b-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine

2-bromo-4,5-dimethoxy-N-(6′,7′-methylenedioxynaphthalen-1-yl)benzamide

(E)-2-(6,7-dimethoxy-isoquinolin-4-yl)-3-(6-nitro-benzo[1,3]dioxol-5-yl)-acrylic acid

Downstream raw materials:

nitidine chloride

oxynitidine

5,6-dihydro-6-methoxynitidine

dihydronitidine

Refernces

• 1、 Zhao, Huai-Bo,Liu, Zhan-Jiang,Song, Jinshuai,Xu, Hai-Chao. "Reagent-Free C?H/N?H Cross-Coupling: Regioselective Synthesis of N-Heteroaromatics from Biaryl Aldehydes and NH3". . p. 12732 - 12735. Retrieved 2017.
• 2、 Jiang, Xunjin,Zeng, Zhixiong,Shi, Dong,Liu, Chenguang,Zhang, Yandong. "Divergent total syntheses of pseudoberberine and nitidine through C[sbnd]H vinylation and switchable 6π electrocyclizations". . . Retrieved 2021.
• 3、 Aravindan, Narasingan,Jeganmohan, Masilamani. "A Short Total Synthesis of Benzophenanthridine Alkaloids via a Rhodium(III)-Catalyzed C-H Ring-Opening Reaction". . p. 14826 - 14843. Retrieved 2021/10/20.