methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate

Base Information

• Chemical Name: methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate
• CAS No.: 1280226-94-9
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.229
• Mol file: 1280226-94-9.mol

Synonyms:

Chemical Property of methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate

There total 1 articles about methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate 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:

3-amino-4-hydroxytoluene (95-84-1) + malonic acid dimethyl ester (108-59-8) → methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate (1280226-94-9)

Guidance literature:

malonic acid dimethyl ester; With potassium hydroxide; In methanol; at 0 - 20 ℃;

3-amino-4-hydroxytoluene; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/adsc.201000647

Reference yield:

4-chlorocinnamaldehyde (1075-77-0) + methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate (1280226-94-9) → methyl 3-(4-chlorophenyl)-8-methyl-1-oxo-1,2,3,4,4a-pentahydrobenzo[d]pyrido[2,1-b]oxazol-2-carboxylate + methyl (2R,3S,4aS)-3-(4-chlorophenyl)-8-methyl-1-oxo-1,2,3,4,4a-pentahydrobenzo[d]pyrido[2,1-b]oxazol-2-carboxylate (1280227-12-4)

Guidance literature:

4-chlorocinnamaldehyde; methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate; With (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; In dichloromethane; at -20 ℃; for 8.5h;

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 12h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/adsc.201000647

Reference yield:

methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate (1280226-94-9) + 3-(4-methylphenyl)acrylaldehyde (1504-75-2) → methyl 8-methyl-1-oxo-3-p-tolyl-1,2,3,4,4a-pentahydrobenzo[d]pyrido[2,1-b]oxazol-2-carboxylate + methyl (2R,3S,4aS)-8-methyl-1-oxo-3-p-tolyl-1,2,3,4,4a-pentahydrobenzo[d]pyrido[2,1-b]oxazol-2-carboxylate (1280227-11-3)

Guidance literature:

methyl 3-(2-hydroxy-5-methylphenylamino)-3-oxopropanoate; 3-(4-methylphenyl)acrylaldehyde; With (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; In dichloromethane; at -20 ℃; for 9.5h;

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 12h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/adsc.201000647

upstream raw materials:

3-amino-4-hydroxytoluene

malonic acid dimethyl ester

Downstream raw materials:

methyl (2R,3S,4aS)-3-(4-chlorophenyl)-8-methyl-1-oxo-1,2,3,4,4a-pentahydrobenzo[d]pyrido[2,1-b]oxazol-2-carboxylate

methyl (2R,3S,4aS)-8-methyl-1-oxo-3-p-tolyl-1,2,3,4,4a-pentahydrobenzo[d]pyrido[2,1-b]oxazol-2-carboxylate