ChemicalBook CAS DataBase List 5-AMINO-2-CHLOROPYRIDINE-4-CARBOXYLIC ACID

5-AMINO-2-CHLOROPYRIDINE-4-CARBOXYLIC ACID synthesis

5synthesis methods

Product Name:5-AMINO-2-CHLOROPYRIDINE-4-CARBOXYLIC ACID
CAS Number:58483-95-7
Molecular formula:C6H5ClN2O2
Molecular Weight:172.57

5-[(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROISONICOTINIC ACID

171178-46-4

58483-95-7

The general procedure for the synthesis of 5-amino-2-chloropyridine-4-carboxylic acid from 5-tert-butoxycarbonylamino-2-chloropyridine-4-carboxylic acid is as follows: 5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid (1.91 g, 7 mmol) was suspended in dichloromethane (200 mL), and trifluoroacetic acid was added slowly dropwise with stirring until the solution became homogeneous (about 5%) 12 mL). The reaction mixture was stirred overnight at room temperature. Subsequently, the reaction mixture was extracted with dilute aqueous ammonia solution and the aqueous phase was acidified with dilute hydrochloric acid to precipitate 5-amino-2-chloropyridine-4-carboxylic acid precipitate (1.05 g, 87% yield). The product was characterized by nuclear magnetic resonance hydrogen spectroscopy (DMSO-d6): δ 9.01 (2H, multiple peaks), 8.03 (1H, single peak), 7.48 (1H, single peak).

171178-46-4
57 suppliers
$51.00/250mg

58483-95-7
158 suppliers
$12.00/250mg

Yield:58483-95-7 87%

Reaction Conditions:

with trifluoroacetic acid in dichloromethane

Steps:

58 4-(3-Bromoanilino)-6-chloropyrido[3,4-d]pyrimidine
5-Amino-2-chloropyridine-4-carboxylic acid. A stirred suspension of 5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid (1.91 g, 7 mmol) in CH₂ Cl₂ (200 mL) is treated slowly with trifluoroacetic acid until homogeneous (ca. 12 mL). The solution is stirred overnight and extracted with dilute NH₄ OH, and the aqueous layer is then acidified with dilute HCl to gave a precipitate of 5-amino-2-chloropyridine-4-carboxylic acid (1.05 g, 87% yield). ¹ H NMR (DMSO) δ 9.01 (2H, m), 8.03 (1H, s), 7.48 (1H, s).

References:

Warner-Lambert Company US5654307, 1997, A

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