7-Chloro-2-ethyl-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione

Base Information

• Chemical Name: 7-Chloro-2-ethyl-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione
• CAS No.: 144155-19-1
• Molecular Formula: C₂₂H₁₇ClF₃NO₂
• Molecular Weight: 419.831
• Mol file: 144155-19-1.mol

Synonyms:

Chemical Property of 7-Chloro-2-ethyl-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Chloro-2-ethyl-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione

There total 8 articles about 7-Chloro-2-ethyl-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione 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:

4-Trifluoromethylbenzaldehyde (455-19-6) → 7-Chloro-2-ethyl-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione (144155-19-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 32 percent / 50percent aq. NaOH / 72 h / Ambient temperature

2: EtONa / ethanol / 6 h / Heating

3: 2 N NaOH / 2 h / Heating

4: 5 N H₂SO₄ / 4.5 h / Heating

5: 90 percent / p-toluenesulfonic acid / benzene / Heating

6: 1.) LDA / 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, a) -65 deg C, 1 h, b) RT, 16 h

7: 10percent aq. HCl / ethanol / Heating

8: 1.) 50percent NaH / 1.) DMF, RT, 1 h, 2.) DMF, 90 deg C, 4 h

With hydrogenchloride; sodium hydroxide; sulfuric acid; sodium ethanolate; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In ethanol; benzene;

DOI:10.1021/jm00097a001

Reference yield:

5-<4-(trifluoromethyl)phenyl>-1,3-cyclohexanedione (55579-69-6) → 7-Chloro-2-ethyl-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione (144155-19-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / p-toluenesulfonic acid / benzene / Heating

2: 1.) LDA / 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, a) -65 deg C, 1 h, b) RT, 16 h

3: 10percent aq. HCl / ethanol / Heating

4: 1.) 50percent NaH / 1.) DMF, RT, 1 h, 2.) DMF, 90 deg C, 4 h

With hydrogenchloride; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In ethanol; benzene;

DOI:10.1021/jm00097a001

Reference yield:

4-(4-trifluoromethylphenyl)but-3-en-2-one (80992-93-4) → 7-Chloro-2-ethyl-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione (144155-19-1)

Guidance literature:

Multi-step reaction with 7 steps

1: EtONa / ethanol / 6 h / Heating

2: 2 N NaOH / 2 h / Heating

3: 5 N H₂SO₄ / 4.5 h / Heating

4: 90 percent / p-toluenesulfonic acid / benzene / Heating

5: 1.) LDA / 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, a) -65 deg C, 1 h, b) RT, 16 h

6: 10percent aq. HCl / ethanol / Heating

7: 1.) 50percent NaH / 1.) DMF, RT, 1 h, 2.) DMF, 90 deg C, 4 h

With hydrogenchloride; sodium hydroxide; sulfuric acid; sodium ethanolate; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In ethanol; benzene;

DOI:10.1021/jm00097a001

upstream raw materials:

5-Chloroisatoic anhydride

cis/trans-4-ethyl-5-<4-(trifluoromethyl)phenyl>-1,3-cyclohexanedione

4-Trifluoromethylbenzaldehyde

5-<4-(trifluoromethyl)phenyl>-1,3-cyclohexanedione

Downstream raw materials:

7-Chloro-1-[(E)-3-dimethylamino-propylimino]-2-ethyl-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one