ChemicalBook CAS DataBase List 3-Fluoropyridine-4-carboxylic acid

3-Fluoropyridine-4-carboxylic acid synthesis

11synthesis methods

Product Name:3-Fluoropyridine-4-carboxylic acid
CAS Number:393-53-3
Molecular formula:C6H4FNO2
Molecular Weight:141.1

124-38-9

393-53-3

3-Fluoropyridine (25 g, 257 mmol) was slowly added dropwise to a solution of tetrahydrofuran (600 mL) containing butyl lithium (270 mmol) and diisopropylamine (27.4 g, 271 mmol) at -78 °C. The reaction mixture was stirred continuously at this temperature for 1 hour. Subsequently, crushed dry ice was added to the reaction system and gradually warmed to room temperature over 1 hour. Upon completion of the reaction, the pH of the reaction solution was adjusted to 5 with an aqueous solution of hydrogen chloride and acidified. The resulting precipitate was collected by filtration and dried. The final 3-fluoroisonicotinic acid (25.2 g, 179 mmol, 70% yield) was obtained as colorless crystals.

124-38-9
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393-53-3
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$10.00/1g

Yield:393-53-3 70%

Reaction Conditions:

Stage #1:3-Fluoropyridine with n-butyllithium;diisopropylamine in tetrahydrofuran at -78; for 1 h;
Stage #2:carbon dioxide in tetrahydrofuran at -78 - 20; for 1 h;
Stage #3: with hydrogenchloride in tetrahydrofuran;water; pH=5

Steps:

1
3-Fluoropyridine (25 g, 257mmol) was added to a solution of butyllithium EPO (270 mmol) and diisopropylamine (27.4 g, 271 mmol) in tetrahydrofuran (600 mL) at - 78°C. After stirring for one hour, crushed dry ice was added to the solution and the solution was warmed to room temperature during one hour. Aqueous hydrogen chloride was added to the solution to acidify the solution to pH 5. The resulting precipitate was filtered and dried. The title compound (25.2 g, 179 mmol, 70%) was obtained as colorless crystal.

References:

MITSUBISHI PHARMA CORPORATION;SANOFI-AVENTIS WO2006/36015, 2006, A2 Location in patent:Page/Page column 121-122

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372-47-4 Synthesis