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

Base Information

• Chemical Name: 7-Chloro-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-2-methyl-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one
• CAS No.: 80092-60-0
• Molecular Formula: C₂₆H₂₇ClF₃N₃O₂
• Molecular Weight: 505.967
• Mol file: 80092-60-0.mol

Synonyms:

Chemical Property of 7-Chloro-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-2-methyl-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Chloro-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-2-methyl-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one

There total 10 articles about 7-Chloro-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-2-methyl-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-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: 22.0%

7-Chloro-10-hydroxy-2-methyl-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione (80092-89-3) + 1-amino-3-(dimethylamino)propane (109-55-7) → 7-Chloro-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-2-methyl-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one (80092-60-0)

Guidance literature:

In ethanol; for 1.5h; Heating;

DOI:10.1021/jm00097a001

Reference yield:

4-Trifluoromethylbenzaldehyde (455-19-6) → 7-Chloro-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-2-methyl-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one (80092-60-0)

Guidance literature:

Multi-step reaction with 9 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: 79 percent / 10percent aq. HCl / ethanol / Heating

8: 33 percent / concd HCl, glacial AcOH / 4 h / 85 °C

9: 22 percent / ethanol / 1.5 h / Heating

With hydrogenchloride; sodium hydroxide; sulfuric acid; sodium ethanolate; toluene-4-sulfonic acid; acetic 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-1-[(E)-3-dimethylamino-propylimino]-10-hydroxy-2-methyl-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one (80092-60-0)

Guidance literature:

Multi-step reaction with 5 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: 79 percent / 10percent aq. HCl / ethanol / Heating

4: 33 percent / concd HCl, glacial AcOH / 4 h / 85 °C

5: 22 percent / ethanol / 1.5 h / Heating

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

DOI:10.1021/jm00097a001

upstream raw materials:

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

1-amino-3-(dimethylamino)propane

4-Trifluoromethylbenzaldehyde

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