3-Quinolinecarbonitrile, 6-(3-chloropropoxy)-4-hydroxy-7-methoxy-

Base Information

• Chemical Name: 3-Quinolinecarbonitrile, 6-(3-chloropropoxy)-4-hydroxy-7-methoxy-
• CAS No.: 380844-30-4
• Molecular Formula: C₁₄H₁₃ClN₂O₃
• Molecular Weight: 292.722
• DSSTox Substance ID: DTXSID201176264
• Mol file: 380844-30-4.mol

Synonyms:380844-30-4;3-Quinolinecarbonitrile, 6-(3-chloropropoxy)-4-hydroxy-7-methoxy-;3-Quinolinecarbonitrile,6-(3-chloropropoxy)-4-hydroxy-7-methoxy-;DTXSID201176264;6-(3-Chloropropoxy)-4-hydroxy-7-methoxy-3-quinolinecarbonitrile

Chemical Property of 3-Quinolinecarbonitrile, 6-(3-chloropropoxy)-4-hydroxy-7-methoxy-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 292.0614700
• Heavy Atom Count: 20
• Complexity: 443

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)NC=C(C2=O)C#N)OCCCCl

Technology Process of 3-Quinolinecarbonitrile, 6-(3-chloropropoxy)-4-hydroxy-7-methoxy-

There total 5 articles about 3-Quinolinecarbonitrile, 6-(3-chloropropoxy)-4-hydroxy-7-methoxy- 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: 47.0%

acetonitrile (75-05-8,26809-02-9) + methyl 5-(3-chloropropoxy)-2-{[(dimethylamino)methylene]amino}-4-methoxybenzoate (380844-28-0) → 6-(3-chloropropoxy)-4-hydroxy-7-methoxy-3-quinolinecarbonitrile (380844-30-4)

Guidance literature:

acetonitrile; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.25h;

methyl 5-(3-chloropropoxy)-2-{[(dimethylamino)methylene]amino}-4-methoxybenzoate; With acetic acid; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1021/jm0102250

Reference yield:

3-hydroxy-4-methoxybenzoate (6702-50-7) → 6-(3-chloropropoxy)-4-hydroxy-7-methoxy-3-quinolinecarbonitrile (380844-30-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 77 percent / tricaprylmethylammonium chloride / acetone / Heating

2.1: 79 percent / nitric acid; AcOH / 2 h / Heating

3.1: 93 percent / Fe; aq. NH₄Cl / methanol / 4 h / Heating

4.1: 8 h / Heating

5.1: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

5.2: 47 percent / AcOH / tetrahydrofuran / -78 - 20 °C

With n-butyllithium; nitric acid; Aliquat 336; iron; ammonium chloride; acetic acid; In tetrahydrofuran; methanol; acetone;

DOI:10.1021/jm0102250

Reference yield:

methyl 3-(3-chloropropoxy)-4-methoxybenzoate (380844-22-4) → 6-(3-chloropropoxy)-4-hydroxy-7-methoxy-3-quinolinecarbonitrile (380844-30-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 79 percent / nitric acid; AcOH / 2 h / Heating

2.1: 93 percent / Fe; aq. NH₄Cl / methanol / 4 h / Heating

3.1: 8 h / Heating

4.1: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

4.2: 47 percent / AcOH / tetrahydrofuran / -78 - 20 °C

With n-butyllithium; nitric acid; iron; ammonium chloride; acetic acid; In tetrahydrofuran; methanol;

DOI:10.1021/jm0102250

upstream raw materials:

acetonitrile

methyl 5-(3-chloropropoxy)-2-{[(dimethylamino)methylene]amino}-4-methoxybenzoate

3-hydroxy-4-methoxybenzoate

methyl 3-(3-chloropropoxy)-4-methoxybenzoate