Process for production of 4-oxoquinoline compound
a production method and compound technology, applied in the preparation of carboxylic compound, bulk chemical production, carboxylic acid halide, etc., can solve the problems of hydrofluoric acid, corroding production facilities, and reducing yield, so as to reduce yield and high value for industrial applications. , the effect of reducing yield
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reference example 1
Synthesis of 3-chloro-2-fluorobenzylzinc bromide
[0210]
[0211]Under an argon atmosphere, a zinc powder (3.18 g) was suspended in tetrahydrofuran (8 ml), 1,2-dibromoethane (0.061 g, 0.32 mmol) and trimethylsilyl chloride (0.071 g, 0.65 mmol) were successively added at 60° C., and the mixture was stirred for 30 min. A solution of 3-chloro-2-fluorobenzyl bromide (7.48 g, 32.5 mmol) in tetrahydrofuran (20 ml) was added dropwise at 60° C. to the solution prepared above. The mixture was further stirred for 1 hr to give a solution of 3-chloro-2-fluorobenzylzinc bromide in tetrahydrofuran.
reference example 2
Synthesis of 3-chloro-2-fluorobenzylzinc chloride
[0212]
[0213]Under an argon atmosphere, a zinc powder (1.44 g) was suspended in tetrahydrofuran (3.6 ml), 1,2-dibromoethane (38 mg) and trimethylsilyl chloride (43 mg) were successively added at 60° C., and the mixture was stirred for 30 min. A solution of 3-chloro-2-fluorobenzyl chloride (3.58 g) in tetrahydrofuran (9 ml) was added dropwise at 60° C. to the solution prepared above. The mixture was further stirred under heating for 1 hr to give a solution of 3-chloro-2-fluorobenzylzinc chloride in tetrahydrofuran.
example 1
Synthesis of 6-(3-chloro-2-fluorobenzyl)-1-((S)-1-hydroxymethyl-2-methylpropyl)-7-methoxy-4-oxo-1,4-dihydroquinoline)-3-carboxylic acid
Step 1
Synthesis of 5-bromo-2,4-dimethoxybenzoic acid
[0214]
[0215]2,4-Dimethoxybenzoic acid (30.0 g) was suspended in acetic acid (180 mL). A bromine (27.6 g) / acetic acid (60 mL) solution was slowly added dropwise to the suspension and, after completion of the dropwise addition, the mixture was stirred at 25° C. for 2 hrs, and the termination of the reaction was confirmed by HPLC. An aqueous solution of sodium sulfite (2.10 g) and water (360 mL) was added dropwise to the reaction mixture. After completion of the dropwise addition, the mixture was stirred at 25° C. for 1 hr. Precipitated crystals were collected by filtration, washed 4 times with water (150 mL), and vacuum dried to give 5-bromo-2,4-dimethoxybenzoic acid as white crystals (41.2 g, 96%).
Step 2
Synthesis of 5-bromo-2,4-dimethoxybenzoic acid chloride
[0216]
[0217]Under a nitrogen atmosphere, 5-...
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