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ChemicalBook CAS DataBase List 2-Amino-3-hydroxypyridine
16867-03-1

2-Amino-3-hydroxypyridine synthesis

10synthesis methods
2-Amino-3-hydroxypyridine was used as reagent in reaction of dimethyl acetylenedicarboxylate and triphenylphosphine to yield functionalized coumarins and 1,4-oxazines.  It was prepared from 2-hydroxy-3-nitropyridine with 10% Pd/C by stirring in methanol for overnight at room temperature.
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Yield:16867-03-1 89%

Reaction Conditions:

palladium-carbon in methanol

Steps:

1 a)Preparation of 2-amino-3-hydroxypyridine
a)Preparation of 2-amino-3-hydroxypyridine To a solution of 2-hydroxy-3-nitropyridine (5 g, 45.4 mmol) in methanol(250 ml) was added 10% Pd/C (1 g). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5% MeOH/CH2Cl2) gave the desired product(3.2 g, 89%). 1H NMR (CD3OD): δ 6.96 (d, 1H), 6.90 (dd, 1H), 6.77 (d, 1H).

References:

SmithKline Beecham Corporation US6218539, 2001, B1

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