2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid

Base Information

• Chemical Name: 2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid
• CAS No.: 1564287-82-6
• Molecular Formula: C₃₅H₃₂N₄O₃
• Molecular Weight: 556.664
• Mol file: 1564287-82-6.mol

Synonyms:2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid

Chemical Property of 2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid

There total 6 articles about 2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid 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: 66.7%

1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinoline-6-carbaldehyde-N-(4-formyl)phenyl-N-phenyl-hydrazone (1529853-62-0) + cyanoacetic acid (372-09-8) → 2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid (1564287-82-6)

Guidance literature:

With ammonium acetate; In acetic acid; at 100 ℃; for 6h;

DOI:10.1016/j.dyepig.2014.01.010

Reference yield:

rac-3-hydroxy-1-phenyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde → 2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid (1564287-82-6)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hydroxide; sodium sulfate / N,N-dimethyl-formamide / 60 - 65 °C

2: isopropyl alcohol / 3 h / 85 °C

3: potassium carbonate / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere

4: ammonium acetate / acetic acid / 6 h / 100 °C

With ammonium acetate; potassium carbonate; sodium sulfate; potassium hydroxide; In acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; 4: |Knoevenagel Condensation;

DOI:10.1016/j.dyepig.2014.01.010

Reference yield:

acetic acid 1-phenyl-1,2,3,4-tetrahydro-quinolin-3-yl ester (3297-78-7) → 2-cyano-3-{4-[1-phenyl-2-(1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinolin-6-methy-lene)hydrazinyl]phenyl}acrylic acid (1564287-82-6)

Guidance literature:

Multi-step reaction with 6 steps

1: trichlorophosphate

2: potassium hydroxide / methanol; water / 0.58 h / Reflux

3: potassium hydroxide; sodium sulfate / N,N-dimethyl-formamide / 60 - 65 °C

4: isopropyl alcohol / 3 h / 85 °C

5: potassium carbonate / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere

6: ammonium acetate / acetic acid / 6 h / 100 °C

With ammonium acetate; potassium carbonate; sodium sulfate; potassium hydroxide; trichlorophosphate; In methanol; water; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; 1: |Vilsmeier-Haack Formylation / 6: |Knoevenagel Condensation;

DOI:10.1016/j.dyepig.2014.01.010

upstream raw materials:

acetic acid 1-phenyl-1,2,3,4-tetrahydro-quinolin-3-yl ester

3-acetyl-1-phenyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde

1-phenyl-3-propoxy-1,2,3,4-tetrahydroquinoline-6-carbaldehyde-N-(4-formyl)phenyl-N-phenyl-hydrazone

cyanoacetic acid