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ChemicalBook CAS DataBase List 3-Amino-2-pyridinecarboxylic acid
1462-86-8

3-Amino-2-pyridinecarboxylic acid synthesis

5synthesis methods
3-NITRO-PYRIDINE-2-CARBOXYLIC ACID

59290-85-6

3-Amino-2-pyridinecarboxylic acid

1462-86-8

(2) Preparation of 3-aminopyridine-2-carboxylic acid: 3-nitropyridine-2-carboxylic acid (2.72 g, 16.2 mmol) and sodium bicarbonate (1.34 g, 16.2 mmol) were dissolved in distilled water (20 mL). The atmosphere in the system was replaced with nitrogen to exclude oxygen. After adding 10% palladium carbon catalyst (1.72 g), the atmosphere in the system was replaced with hydrogen and the reaction was stirred at room temperature for 50 hours. After completion of the reaction, the pH of the reaction solution was adjusted to weakly acidic by adding 1N aqueous hydrochloric acid. The solvent was removed by distillation under reduced pressure and a small amount of ethanol and ethyl acetate was added to the residue and the resulting precipitate was collected by filtration. The filtrate was concentrated to afford the target product 3-aminopyridine-2-carboxylic acid (1.50 g, 67% yield) as a light yellow solid.

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Yield:1462-86-8 67%

Reaction Conditions:

Stage #1:3-nitropyridine-2-carboxylic acid with hydrogen;sodium hydrogencarbonate;palladium 10% on activated carbon in water at 20; for 50 h;
Stage #2: with hydrogenchloride in water

Steps:

268.2
(2) Manufacture of 3-aminopyridine-2-carboxylic acid 3-nitropyridine-2-carboxylic acid (2.72 g, 16.2 mmol) and sodium hydrogencarbonate (1.34 g, 16.2 mmol) were dissolved in distilled water (20 mL), and the atmosphere in the system was replaced by nitrogen. After adding 10% palladium charcoal (1.72 g), the atmosphere in the system was replaced by hydrogen, and the mixture stirred at room temperature for 50 hours. 1N hydrochloric acid aqueous solution was added, and the pH of the reaction solution was adjusted to weak acidity. The solvent was distilled off under reduced pressure, a small amount of ethanol and ethyl acetate were added to the residue, and the precipitate produced was filtered off. The filtrate was concentrated, and the target substance (1.50 g, 67%) was thus obtained as a light yellow solid.

References:

Banyu Pharmaceutical Co., Ltd. US2005/182045, 2005, A1 Location in patent:Page/Page column 74

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