Réaction #1897

Équation de réaction

2-amino-5-bromophenyl-2-pyridylketone

methanol

sodium borohydride

→

2-amino-5-bromo-α-(2-pyridyl)benzyl alcohol

Conditions de réaction

Traitement

1. 1
   AutreThe solvent methanol was evaporated off under reduced pressure
2. 2
   workup.ADDITIONThe residue was treated with an aqueous solution of hydrochloric acid
3. 3
   Extractionextracted with ethyl acetate
4. 4
   LavageThe ethyl acetate layer was washed with water
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1)

Mode opératoire

In 100 ml of methanol was dissolved 10 g of 2-amino-5-bromophenyl-2-pyridylketone. To the solution was added 1.7 g of sodium borohydride and stirred for 30 minutes. The solvent methanol was evaporated off under reduced pressure. The residue was treated with an aqueous solution of hydrochloric acid. The decomposed residue was then neutralized with 200 ml of a sodium bicarbonate aqueous solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 2-amino-5-bromo-α-(2-pyridyl)benzyl alcohol (9.0 g) as prisms, m.p. 104°-105° C.

Source