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

Base Information

Chemical Name:6-(3-chloro-2-fluorobenzyl)-1-cyclopropyl-5-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
CAS No.:1333140-98-9
Molecular Formula:C₂₀H₁₅ClFNO₄
Molecular Weight:387.795
Hs Code.:

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

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

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

There total 10 articles about 6-(3-chloro-2-fluorobenzyl)-1-cyclopropyl-5-hydroxy-4-oxo-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: 32.0%

: 1333141-08-4
6-(3-chloro-2-fluorobenzyl)-1-cyclopropyl-5-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

: 1333140-98-9
6-(3-chloro-2-fluorobenzyl)-1-cyclopropyl-5-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Guidance literature:: 6-(3-chloro-2-fluorobenzyl)-1-cyclopropyl-5-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; With sodium hydroxide; In 1,4-dioxane; at 80 ℃;

With hydrogenchloride; water; In 1,4-dioxane; pH=2;
DOI:10.1016/j.bmc.2011.06.020

Reference yield:

: 1333140-87-6
methyl 3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoate

: 1333140-98-9
6-(3-chloro-2-fluorobenzyl)-1-cyclopropyl-5-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

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

1.2: pH 2

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

2.2: 50 °C

3.1: tetrahydrofuran / 3 h / 50 °C

4.1: tetrahydrofuran / 50 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 60 - 90 °C

6.1: lithium hydroxide / 1,4-dioxane; water / 3 h / 50 °C

6.2: pH 2

7.1: sodium hydroxide / 1,4-dioxane / 80 °C

7.2: pH 2

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2011.06.020

Reference yield:

: 1333140-88-7
3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoic acid

: 1333140-98-9
6-(3-chloro-2-fluorobenzyl)-1-cyclopropyl-5-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 °C

1.2: 50 °C

2.1: tetrahydrofuran / 3 h / 50 °C

3.1: tetrahydrofuran / 50 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 60 - 90 °C

5.1: lithium hydroxide / 1,4-dioxane; water / 3 h / 50 °C

5.2: pH 2

6.1: sodium hydroxide / 1,4-dioxane / 80 °C

6.2: pH 2

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2011.06.020