6-chloro-8-((3-(dimethylamino)propyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one

Base Information

Chemical Name:6-chloro-8-((3-(dimethylamino)propyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one
CAS No.:1621457-94-0
Molecular Formula:C₂₁H₂₂ClN₃O₅
Molecular Weight:431.876
Hs Code.:

Synonyms:6-chloro-8-((3-(dimethylamino)propyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one

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Chemical Property of 6-chloro-8-((3-(dimethylamino)propyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one

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Technology Process of 6-chloro-8-((3-(dimethylamino)propyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one

There total 5 articles about 6-chloro-8-((3-(dimethylamino)propyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one 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: 82.0%

: 1621457-83-7
8-bromo-6-chloro-2-(3-methoxy-2-nitrophenyl)chromone

: 109-55-7
1-amino-3-(dimethylamino)propane

: 1621457-94-0
6-chloro-8-((3-(dimethylamino)propyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one

Guidance literature:: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In tetrahydrofuran; at 80 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.ejmech.2014.07.018

Reference yield:

: 15865-57-3
2-nitro-3-methoxybenzoyl chloride

: 1621457-94-0
6-chloro-8-((3-(dimethylamino)propyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / toluene / 2.5 h / 20 °C / Cooling with ice

2: potassium hydroxide / pyridine / 0.5 h / 100 °C / Microwave irradiation

3: sulfuric acid / ethanol / 0.5 h / 100 °C / Microwave irradiation

4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; caesium carbonate / tetrahydrofuran / 80 °C / Inert atmosphere

With pyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sulfuric acid; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; potassium hydroxide; In tetrahydrofuran; pyridine; ethanol; toluene; 4: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.ejmech.2014.07.018

Reference yield:

: 4920-80-3
3-methoxy-2-nitrobenzoic acid

: 1621457-94-0
6-chloro-8-((3-(dimethylamino)propyl)amino)-2-(3-methoxy-2-nitrophenyl)-4H-chromen-4-one

Guidance literature:: Multi-step reaction with 5 steps

1: thionyl chloride / toluene / 20 h / Reflux

2: pyridine / toluene / 2.5 h / 20 °C / Cooling with ice

3: potassium hydroxide / pyridine / 0.5 h / 100 °C / Microwave irradiation

4: sulfuric acid / ethanol / 0.5 h / 100 °C / Microwave irradiation

5: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; caesium carbonate / tetrahydrofuran / 80 °C / Inert atmosphere

With pyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; thionyl chloride; sulfuric acid; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; potassium hydroxide; In tetrahydrofuran; pyridine; ethanol; toluene; 5: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.ejmech.2014.07.018