6-(3-chloro-2-fluorobenzyl)-5-hydroxy-4-oxo-1-m-tolyl-1,4-dihydroquinoline-3-carboxylic acid

Base Information

• Chemical Name: 6-(3-chloro-2-fluorobenzyl)-5-hydroxy-4-oxo-1-m-tolyl-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 1338560-91-0
• Molecular Formula: C₂₄H₁₇ClFNO₄
• Molecular Weight: 437.855
• Mol file: 1338560-91-0.mol

Synonyms:6-(3-chloro-2-fluorobenzyl)-5-hydroxy-4-oxo-1-m-tolyl-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property of 6-(3-chloro-2-fluorobenzyl)-5-hydroxy-4-oxo-1-m-tolyl-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(3-chloro-2-fluorobenzyl)-5-hydroxy-4-oxo-1-m-tolyl-1,4-dihydroquinoline-3-carboxylic acid

There total 9 articles about 6-(3-chloro-2-fluorobenzyl)-5-hydroxy-4-oxo-1-m-tolyl-1,4-dihydroquinoline-3-carboxylic 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:

C25H19ClFNO4 (1338561-35-5) → 6-(3-chloro-2-fluorobenzyl)-5-hydroxy-4-oxo-1-m-tolyl-1,4-dihydroquinoline-3-carboxylic acid (1338560-91-0)

Guidance literature:

C₂₅H₁₉ClFNO₄; With boron tribromide; In dichloromethane; at -40 - 20 ℃;

With water; In dichloromethane; Cooling with ice;

DOI:10.1016/j.bmc.2011.07.037

Reference yield:

1-(bromomethyl)-3-chloro-2-fluorobenzene (85070-47-9) → 6-(3-chloro-2-fluorobenzyl)-5-hydroxy-4-oxo-1-m-tolyl-1,4-dihydroquinoline-3-carboxylic acid (1338560-91-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: chloro-trimethyl-silane; ethylene dibromide; zinc / tetrahydrofuran / 1 h / 60 °C / Inert atmosphere

1.2: 60 °C / Inert atmosphere; Reflux

2.1: lithium hydroxide / tetrahydrofuran; water / 3 h / 50 °C

2.2: pH 2 / Cooling with ice

3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 °C

3.2: 60 °C

3.3: pH 6 - 7

4.1: tetrahydrofuran / 3 h / 50 °C

5.1: tetrahydrofuran / 60 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 90 °C

7.1: N,N-dimethyl-formamide; toluene / Reflux

7.2: pH 2 / Cooling with ice

8.1: boron tribromide / dichloromethane / -40 - 20 °C

8.2: Cooling with ice

With chloro-trimethyl-silane; boron tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylene dibromide; 1,1'-carbonyldiimidazole; lithium hydroxide; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2011.07.037

Reference yield:

methyl 3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoate (1333140-87-6) → 6-(3-chloro-2-fluorobenzyl)-5-hydroxy-4-oxo-1-m-tolyl-1,4-dihydroquinoline-3-carboxylic acid (1338560-91-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium hydroxide / tetrahydrofuran; water / 3 h / 50 °C

1.2: pH 2 / Cooling with ice

2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 °C

2.2: 60 °C

2.3: pH 6 - 7

3.1: tetrahydrofuran / 3 h / 50 °C

4.1: tetrahydrofuran / 60 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 90 °C

6.1: N,N-dimethyl-formamide; toluene / Reflux

6.2: pH 2 / Cooling with ice

7.1: boron tribromide / dichloromethane / -40 - 20 °C

7.2: Cooling with ice

With boron tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2011.07.037

upstream raw materials:

1-(bromomethyl)-3-chloro-2-fluorobenzene

methyl 3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoate

3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoic acid

methyl 3-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorophenyl)-3-oxopropanoate