ChemicalBook CAS DataBase List 3-Amino-4-iodopyridine

3-Amino-4-iodopyridine synthesis

4synthesis methods

Product Name:3-Amino-4-iodopyridine
CAS Number:105752-11-2
Molecular formula:C5H5IN2
Molecular Weight:220.01

N-(4-IODO-PYRIDIN-3-YL)-2,2-DIMETHYL-PROPIONAMIDE

113975-32-9

105752-11-2

General procedure for the synthesis of 3-amino-4-iodopyridine from N-(4-iodo-3-pyridinyl)-2,2-dimethylpropanamide: N-(4-iodo-3-pyridinyl)-2,2-dimethylpropanamide (20.00 g, 65.76 mmol) was placed in a 2 L round-bottomed flask, and 24% sulfuric acid aqueous solution (640 mL) was added. The mixture was carefully heated to 100 °C and kept for 4 hours. The progress of the reaction was monitored by analytical HPLC. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was slowly adjusted to 7-8 with 4 N NaOH solution (~700 mL).Subsequently, saturated sodium bicarbonate solution was added and extracted with dichloromethane (3 x 500 mL). The organic phases were combined and concentrated to give 3-amino-4-iodopyridine (13.3 g, 92% yield).

113975-32-9
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$45.00/50mg

105752-11-2
203 suppliers
$37.00/1g

Yield:105752-11-2 92%

Reaction Conditions:

Stage #1:2,2-dimethyl-N-(4-iodo-3-pyridinyl)propanamide with sulfuric acid in water at 100; for 4 h;
Stage #2: with sodium hydroxide in water; pH=7 - 8 at 20;Product distribution / selectivity;

Steps:

4.1
iV-(4-Iodo-pyridin-3-yl)-2,2-dimethyl-propionamide (20.00 g, 65.76 mmol) was charged to a 2 L round-bottom flask and 24% sulfuric acid in water (640 mL) was added carefully. The mixture was heated to 100 °C for 4 hours. The reaction was determined complete by analyitical HPLC. The mixture was allowed to cool to room temperature and then carefully adjusted to pH 7-8 with 4Ν NaOH (approximately 700 mL). Saturated sodium bicarbonate was added to the mixture and the product extracted into dichloromethane (3 X 500 mL). The organic layers were combined and concentrated to give 3-amino-4-iodo- pyridine (13.3 g, 92%).

References:

AXYS PHARMACEUTICALS, INC. WO2006/86609, 2006, A2 Location in patent:Page/Page column 154

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239137-39-4 Synthesis