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ChemicalBook CAS DataBase List 4-Amino-2-ethoxypyridine
89943-12-4

4-Amino-2-ethoxypyridine synthesis

8synthesis methods
4-Amino-2-bromopyridine

7598-35-8

4-Amino-2-ethoxypyridine

89943-12-4

The general procedure for the synthesis of 2-ethoxy-4-aminopyridine from 4-amino-2-bromopyridine is as follows: 1. 2-Bromo-4-aminopyridine (4 g), solid sodium hydroxide (4 g) and ethanol (15 ml) were placed in a reactor and heated at 160°C for 6 hrs followed by cooling to room temperature. 2. Water was added to the reaction mixture and then the solvent was partially evaporated under reduced pressure. 3. The mixture was extracted using ether and the solvent was subsequently evaporated to give a clarified oily product of 2-ethoxy-4-aminopyridine (164 g, 76% yield). 4. The oily product slowly crystallized to form colorless needle-like crystals with a melting point of 88-89 °C. The product was extracted with ether and subsequently evaporated.

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Yield: 76%

Reaction Conditions:

with sodium hydroxide in ethanol;water

Steps:

19.l f
l) 2-Ethoxy-4-aminopyridine (Den Hertog, Kolder and Combe, 1951) 2-Bromo-4-aminopyridine (4 g). solid sodium hydroxide (4 g) and ethanol (15 ml) were heated in a bomb at 160° C. for 6 hours and allowed to cool. Water was then added and the solvent partially removed under reduced pressure. The mixture was then extracted with ether and the solvent removed, leaving a clear oil of 2-Ethoxy-4-aminopyridine (164 g, 76%) which slowly crystallized into colourless needles, m.p. 88-89° C.

References:

Polychip Pharmaceuticals Pty Ltd;The University of Sydney US5929082, 1999, A

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