methyl 2-hydroxy-3-(N,N-dimethylamino)benzoate

Base Information

• Chemical Name: methyl 2-hydroxy-3-(N,N-dimethylamino)benzoate
• CAS No.: 1616786-26-5
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.218
• Mol file: 1616786-26-5.mol

Synonyms:methyl 2-hydroxy-3-(N,N-dimethylamino)benzoate

Chemical Property of methyl 2-hydroxy-3-(N,N-dimethylamino)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of methyl 2-hydroxy-3-(N,N-dimethylamino)benzoate

There total 3 articles about methyl 2-hydroxy-3-(N,N-dimethylamino)benzoate 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: 85.8%

methyl 3-aminosalicylate (35748-34-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → methyl 2-hydroxy-3-(N,N-dimethylamino)benzoate (1616786-26-5)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 2h;

Reference yield:

methyl 3-(N,N-dimethylamino)benzoate-N-oxide (1616786-25-4) → methyl 2-hydroxy-3-(N,N-dimethylamino)benzoate (1616786-26-5) + methyl 3-(dimethylamino)-4-hydroxybenzoate (316158-20-0)

Guidance literature:

methyl 3-(N,N-dimethylamino)benzoate-N-oxide; With trifluoroacetic anhydride; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 0 ℃; for 0.25h; Overall yield = 38 %; Inert atmosphere;

DOI:10.1021/ol501813s

Reference yield:

3-(dimethylamino)benzoic acid methyl ester (16518-64-2) → methyl 2-hydroxy-3-(N,N-dimethylamino)benzoate (1616786-26-5) + methyl 3-(dimethylamino)-4-hydroxybenzoate (316158-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 23 °C / Inert atmosphere

2.1: trifluoroacetic anhydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 0.25 h / -78 - 0 °C / Inert atmosphere

With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In dichloromethane;

DOI:10.1021/ol501813s

upstream raw materials:

methyl 3-(N,N-dimethylamino)benzoate-N-oxide

3-(dimethylamino)benzoic acid methyl ester

methyl 3-aminosalicylate

formaldehyd

Refernces

• 1、 Lewis, Robert S.,Wisthoff, Michael F.,Grissmerson,Chain, William J.. "Metal-free functionalization of N, N-dialkylanilines via temporary oxidation to N, N-dialkylaniline N-oxides and group transfer". supporting information. p. 3832 - 3835. Retrieved 2014/08/05.