5-<4-(quinolin-2-ylmethoxy)phenyl>-3,3-tetramethylenepentanenitrile

Base Information

• Chemical Name: 5-<4-(quinolin-2-ylmethoxy)phenyl>-3,3-tetramethylenepentanenitrile
• CAS No.: 129650-11-9
• Molecular Formula: C₂₅H₂₆N₂O
• Molecular Weight: 370.494
• Mol file: 129650-11-9.mol

Synonyms:5-<4-(quinolin-2-ylmethoxy)phenyl>-3,3-tetramethylenepentanenitrile

Chemical Property of 5-<4-(quinolin-2-ylmethoxy)phenyl>-3,3-tetramethylenepentanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-<4-(quinolin-2-ylmethoxy)phenyl>-3,3-tetramethylenepentanenitrile

There total 9 articles about 5-<4-(quinolin-2-ylmethoxy)phenyl>-3,3-tetramethylenepentanenitrile 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: 79.0%

2-(1-{2-[4-(Quinolin-2-ylmethoxy)-phenyl]-ethyl}-cyclopentyl)-acetamide (129650-10-8) → 5-<4-(quinolin-2-ylmethoxy)phenyl>-3,3-tetramethylenepentanenitrile (129650-11-9)

Guidance literature:

With pyridine; methanesulfonyl chloride; for 3.5h; Ambient temperature;

DOI:10.1021/jm00172a024

Reference yield:

3,3-tetramethylene glutaric anhydride (5662-95-3) → 5-<4-(quinolin-2-ylmethoxy)phenyl>-3,3-tetramethylenepentanenitrile (129650-11-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / AlCl₃ / nitrobenzene; various solvent(s) / 2 h

2: 96 percent / H₂ / 10percent Pd/C / acetic acid / 1.5 h / 2327.2 Torr

3: 72 percent / 47-59percent aq. HBr / acetic acid / 2.5 h / Heating

4: 90 percent / concd. H₂SO₄ / 2 h / Heating

5: 44 percent / K₂CO₃ / acetone; dimethylformamide / 72 h / Heating

6: 95 percent / 0.5 M NaOH / ethanol / 4 h / Heating

7: 1.) carbonyldiimidazole (CDI), 2.) concd. NH₄OH / 1.) CH₂Cl₂, 1 h, 2.) THF, 18 h

8: 79 percent / methanesulfonyl chloride, pyridine / 3.5 h / Ambient temperature

With pyridine; ammonium hydroxide; sodium hydroxide; aluminium trichloride; sulfuric acid; hydrogen bromide; hydrogen; potassium carbonate; methanesulfonyl chloride; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In ethanol; acetic acid; nitrobenzene; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00172a024

Reference yield:

5-(4-methoxyphenyl)-5-oxo-3,3-tetramethylenepentanoic acid (403481-48-1) → 5-<4-(quinolin-2-ylmethoxy)phenyl>-3,3-tetramethylenepentanenitrile (129650-11-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / H₂ / 10percent Pd/C / acetic acid / 1.5 h / 2327.2 Torr

2: 72 percent / 47-59percent aq. HBr / acetic acid / 2.5 h / Heating

3: 90 percent / concd. H₂SO₄ / 2 h / Heating

4: 44 percent / K₂CO₃ / acetone; dimethylformamide / 72 h / Heating

5: 95 percent / 0.5 M NaOH / ethanol / 4 h / Heating

6: 1.) carbonyldiimidazole (CDI), 2.) concd. NH₄OH / 1.) CH₂Cl₂, 1 h, 2.) THF, 18 h

7: 79 percent / methanesulfonyl chloride, pyridine / 3.5 h / Ambient temperature

With pyridine; ammonium hydroxide; sodium hydroxide; sulfuric acid; hydrogen bromide; hydrogen; potassium carbonate; methanesulfonyl chloride; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In ethanol; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00172a024

upstream raw materials:

2-(1-{2-[4-(Quinolin-2-ylmethoxy)-phenyl]-ethyl}-cyclopentyl)-acetamide

3,3-tetramethylene glutaric anhydride

5-(4-hydroxyphenyl)-3,3-tetramethylenepentanoic acid

5-(4-methoxyphenyl)-3,3-tetramethylenepentanoic acid

Downstream raw materials:

2-(4-{2-[1-(1H-Tetrazol-5-ylmethyl)-cyclopentyl]-ethyl}-phenoxymethyl)-quinoline