N-Methoxy-2-naphthamide

Base Information

• Chemical Name: N-Methoxy-2-naphthamide
• CAS No.: 76749-35-4
• Molecular Formula: C12H11 N O2
• Molecular Weight: 201.225
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID10227564
• Nikkaji Number: J3.648.889A
• Wikidata: Q83107360
• ChEMBL ID: CHEMBL154442
• Mol file: 76749-35-4.mol

Synonyms:N-Methoxy-2-naphthamide;76749-35-4;2-Naphtho-O-methylhydroxamic acid;N-methoxynaphthalene-2-carboxamide;2-Naphthohydroxamic acid, O-methyl-;2-Naphthalenecarboxamide, N-methoxy-;N-Methoxy-2-naphthalenecarboxamide;CHEMBL154442;SCHEMBL13527515;DTXSID10227564;N-methoxy-2-naphthylcarboxylic amide;AKOS009092466;SB77729;LS-95340;J3.648.889A;Z188880124

Chemical Property of N-Methoxy-2-naphthamide

Chemical Property:

• PSA: 41.82000
• Density: 1.181g/cm³
• LogP: 2.70580
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 230

Purity/Quality:

99%min ^*data from raw suppliers

N-Methoxy-2-naphthamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CONC(=O)C1=CC2=CC=CC=C2C=C1

Technology Process of N-Methoxy-2-naphthamide

There total 5 articles about N-Methoxy-2-naphthamide 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-methoxylamine hydrochloride (593-56-6) + 2-naphthaloyl chloride (2243-83-6) → 2-methoxy-3-phenylbenzo[g]isoquinolin-1(2H)-one (76749-35-4)

Guidance literature:

With potassium carbonate; In water; ethyl acetate; at 0 - 20 ℃; for 16h; Under an atmosphere of argon;

DOI:10.1021/ja109676d

Reference yield:

N-methoxylamine hydrochloride (593-56-6) + naphthalene-2-carboxylate (93-09-4) → 2-methoxy-3-phenylbenzo[g]isoquinolin-1(2H)-one (76749-35-4)

Guidance literature:

naphthalene-2-carboxylate; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3.5h;

N-methoxylamine hydrochloride; With potassium carbonate; In water; ethyl acetate; at 20 ℃; for 20h;

DOI:10.1021/acs.orglett.6b01566

Reference yield:

naphthalene-2-carboxylate (93-09-4) → 2-methoxy-3-phenylbenzo[g]isoquinolin-1(2H)-one (76749-35-4)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C

2: potassium carbonate / ethyl acetate; water / 8 h / 0 - 20 °C

With oxalyl dichloride; potassium carbonate; N,N-dimethyl-formamide; In dichloromethane; water; ethyl acetate;

DOI:10.1021/jo5020307

upstream raw materials:

N-methoxylamine hydrochloride

2-naphthaloyl chloride

naphthalene-2-carboxylate

O-Methylhydroxylamin

Downstream raw materials:

(E)-3-styryl-2-naphthamide

1,2-diphenylbenzo[f]-isoquinolin-4(3H)-one

3,4-diphenylbenzo[g]isoquinolin-1(2H)-one

2-methoxy-3-phenylbenzo[g]isoquinolin-1(2H)-one

Refernces

• 1、 Yan, Kelu,Jin, Junbin,Kong, Yong,Li, Bin,Wang, Baiquan. "Palladium-Catalyzed Inert C?H Bond Activation and Cyclocarbonylation of Isoquinolones with Carbon Dioxide Leading to Isoindolo[2,1-b]isoquinoline-5,7-Diones". supporting information. p. 3080 - 3085. Retrieved 2019/05/21.
• 2、 Chen, Zenghua,Hu, Le'an,Zeng, Fanyun,Zhu, Ranran,Zheng, Shasha,Yu, Qingzhen,Huang, Jianhui. "Selective mono-alkylation of N-methoxybenzamides". supporting information. p. 4258 - 4261. Retrieved 2017/04/21.