N-[(4-bromo-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]acetamide

Base Information

• Chemical Name: N-[(4-bromo-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]acetamide
• CAS No.: 1008531-78-9
• Molecular Formula: C₁₉H₁₆BrNO₂
• Molecular Weight: 370.246
• Mol file: 1008531-78-9.mol

Synonyms:N-[(4-bromo-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]acetamide

Chemical Property of N-[(4-bromo-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(4-bromo-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]acetamide

There total 3 articles about N-[(4-bromo-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]acetamide 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: 96.0%

acetamide (60-35-5) + 4-bromo-benzaldehyde (1122-91-4) + β-naphthol (135-19-3) → N-[(4-bromo-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]acetamide (1008531-78-9)

Guidance literature:

With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium hydrogensulfate; In 1,2-dichloro-ethane; at 20 ℃; for 2.5h;

DOI:10.1080/00397910903537356

Reference yield: 95.0%

4-bromo-benzaldehyde (1122-91-4) + acetonitrile (75-05-8,26809-02-9) + β-naphthol (135-19-3) → N-[(4-bromo-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]acetamide (1008531-78-9)

Guidance literature:

4-bromo-benzaldehyde; acetonitrile; β-naphthol; With phosphorus pentaoxide; Hexamethyldisiloxane; at 20 ℃; for 3h;

With water; Further stages.; cooling;

DOI:10.1080/00397910802213778

Reference yield:

4-bromobenzenemethanol (873-75-6) → N-[(4-bromo-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]acetamide (1008531-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 2-hydroxy-N,N,N-trimethyl ethanaminium peroxydisulfate / neat (no solvent) / 0.5 h / 70 °C / Green chemistry

2: choline hydrogen sulphate / neat (no solvent) / 0.17 h / 70 °C / Green chemistry

With choline hydrogen sulphate; 2-hydroxy-N,N,N-trimethyl ethanaminium peroxydisulfate; In neat (no solvent);

DOI:10.1039/c4nj02295e

upstream raw materials:

acetamide

4-bromo-benzaldehyde

β-naphthol

acetonitrile

Downstream raw materials:

[1-(4-bromophenyl)-1,2-dihydro-3H-naphtho[1,2-e][1,3]oxazine-3-ylidene]malonaldehyde

Refernces

• 1、 Bamoharram, Fatemeh F.,Heravi, Majid M.,Roshani, Mina,Charkhi, Mohammad J. Sane. "Multicomponent, solvent-free synthesis of 1-Amidoalkyl-2-naphthols in the presence of H3+xPMo12-xVxO40 heteropolyacids as recyclable and green catalysts". . p. 523 - 528. Retrieved 2011.
• 2、 Mistry, Sunil R.,Joshi, Rikesh S.,Maheria, Kalpana C.. "Zeolite H-Bea catalysed multicomponent reaction: One-Pot synthesis of amidoalkyl naphthols - Biologically active drug-like molecules". . p. 427 - 432. Retrieved 2011.
• 3、 Shaterian, Hamid Reza,Yarahmadi, Hossein,Ghashang, Majid. "An efficient, simple and expedition synthesis of 1-amidoalkyl-2-naphthols as 'drug like' molecules for biological screening". . p. 788 - 792. Retrieved 2008.
• 4、 Zali, Abbas,Shokrolahi, Arash. "Nano-sulfated zirconia as an efficient, recyclable and environmentally benign catalyst for one-pot three component synthesis of amidoalkyl naphthols". . p. 269 - 272. Retrieved 2012.
• 5、 Niralwad, Kirti S.,Shingate, Bapurao B.,Shingare, Murlidhar S.. "1-Hexanesulphonic acid sodium salt promoted the one-pot synthesis of amidoalkyl naphthols under microwave-irradiation". . p. 551 - 554. Retrieved 2011.
• 6、 Anary-Abbasinejad, Mohammad,Hassanabadi, Alireza,Kamali-Gharamaleki, Maryam,Saidipoor, Azimeh,Anaraki-Ardakani, Hossein. "Three-component reaction between 2-naphthol, aromatic aldehydes and acetonitrile in the presence of chlorosulfonic acid yields 1-(acetylamino (aryl)methyl)-2-naphthols". . p. 644 - 646. Retrieved 2007.
• 7、 Zare, Abdolkarim. "Solvent-free condensation of 2-naphthol with aromatic aldehydes and acetamide/urea to 1-amidoalkyl-2-naphthols". . p. 82 - 90. Retrieved 2012.
• 8、 Moosavi-Zare, Ahmad Reza,Goudarziafshar, Hamid,Nooraei, Fatemeh. "Preparation and characterization of nano-Co-[4-chlorophenyl-salicylaldimine-methyl pyranopyrazole]Cl2 as a new Schiff base complex and catalyst for the solvent-free synthesis of 1-amidoalkyl-2-naphthols". . . Retrieved 2020.
• 9、 Zare, Abdolkarim,Hasaninejad, Alireza,Rostami, Esmael,Moosavi-Zare, Ahmad Reza,Pishahang, Nasrin,Roshankar, Mehrnoosh,Khedri, Fatemeh,Khedri, Maasoomeh. "An efficient solvent-free protocol for the synthesis of 1-amidoalkyl-2-naphthols using silica-supported molybdatophosphoric acid". . p. 1162 - 1169. Retrieved 2010.
• 10、 Luo, Jun,Zhang, Qiang. "A one-pot multicomponent reaction for synthesis of 1-amidoalkyl- 2-naphthols catalyzed by PEG-based dicationic acidic ionic liquids under solvent-free conditions". . p. 923 - 930. Retrieved 2011.