4-(DiMethylaMino)benzoic Acid 6-Acetyl-2,3-diMethoxyphenyl Ester

Base Information

• Chemical Name: 4-(DiMethylaMino)benzoic Acid 6-Acetyl-2,3-diMethoxyphenyl Ester
• CAS No.: 1205548-01-1
• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.379
• Mol file: 1205548-01-1.mol

Synonyms:6-acetyl-2,3-dimethoxyphenyl 4-(dimethylamino)benzoate

Chemical Property of 4-(DiMethylaMino)benzoic Acid 6-Acetyl-2,3-diMethoxyphenyl Ester

Chemical Property:

• Solubility.: Dichloromethane, Methanol

Purity/Quality:

4-(Dimethylamino)benzoicAcid6-Acetyl-2,3-dimethoxyphenylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 4-(Dimethylamino)benzoic Acid 6-Acetyl-2,3-dimethoxyphenyl Ester is a reactant used in the preparation of 7,8-Dihydroxyflavone (D452830) derivatives which promote neurogenesis and exhibits potent antidepressant effect.

Technology Process of 4-(DiMethylaMino)benzoic Acid 6-Acetyl-2,3-diMethoxyphenyl Ester

There total 1 articles about 4-(DiMethylaMino)benzoic Acid 6-Acetyl-2,3-diMethoxyphenyl Ester 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: 87.0%

4-(dimethylamino)benzoyl chloride (4755-50-4) + 2'-hydroxy-3',4'-dimethoxyacetophenone (5396-18-9) → 6-acetyl-2,3-dimethoxyphenyl 4-(dimethylamino)benzoate (1205548-01-1)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmc.2013.10.012

Reference yield:

6-acetyl-2,3-dimethoxyphenyl 4-(dimethylamino)benzoate (1205548-01-1) → 1-(4-(dimethylamino)phenyl)-3-(2-hydroxy-3,4-dimethoxyphenyl)propane-1,3-dione (1205548-02-2)

Guidance literature:

With pyridine; potassium hydroxide; at 50 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm101206p

Reference yield:

6-acetyl-2,3-dimethoxyphenyl 4-(dimethylamino)benzoate (1205548-01-1) → 2-(4-(dimethylamino)phenyl)-7,8-dihydroxy-4H-chromen-4-one

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; potassium hydroxide / 12 h / 50 °C

2: acetic acid; sulfuric acid / 1 - 3 h / Reflux

3: boron tribromide / dichloromethane / 20 °C / Cooling with ice

With pyridine; sulfuric acid; boron tribromide; acetic acid; potassium hydroxide; In dichloromethane; 1: |Baker-Venkataraman Rearrangement;

DOI:10.1016/j.bmc.2013.10.012

upstream raw materials:

4-(dimethylamino)benzoyl chloride

2'-hydroxy-3',4'-dimethoxyacetophenone

Downstream raw materials:

1-(4-(dimethylamino)phenyl)-3-(2-hydroxy-3,4-dimethoxyphenyl)propane-1,3-dione

2-(4-(dimethylamino)phenyl)-7,8-dimethoxy-4H-chromen-4-one

Refernces

• 1、 Bernard-Gauthier, Vadim,Boudjemeline, Mehdi,Rosa-Neto, Pedro,Thiel, Alexander,Schirrmacher, Ralf. "Towards tropomyosin-related kinase B (TrkB) receptor ligands for brain imaging with PET: Radiosynthesis and evaluation of 2-(4-[18F] fluorophenyl)-7,8-dihydroxy-4H-chromen-4-one and 2-(4-([N-methyl- 11C]-dimethylamino)phenyl)-7,8-dihydroxy-4H-chromen-4-one". . p. 7816 - 7829. Retrieved 2014/01/06.