Reaktionsgleichung
NC1C=CC(Br)=CC=1C1C([C:15]([C:17]2[C:22]([C:23]3[CH:28]=[C:27]([Br:29])[CH:26]=[CH:25][C:24]=3[NH2:30])=[CH:21][CH:20]=[CH:19][N:18]=2)=O)=NC=CC=1.[BH4-].[Na+].C[OH:34]>>[NH2:30][C:24]1[CH:25]=[CH:26][C:27]([Br:29])=[CH:28][C:23]=1[CH:22]([OH:34])[C:17]1[CH:15]=[CH:21][CH:20]=[CH:19][N:18]=1Komponenten
Versuchsvorschrift
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 hyrochloric acid. The decomposed residue was then neutralized with 200 ml of a sodium bicarbonate aqeous 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.
Aufarbeitung
- customThe solvent methanol was evaporated off under reduced pressure
- additionThe residue was treated with an aqueous solution of hyrochloric acid
- extractionextracted with ethyl acetate
- washThe ethyl acetate layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-c19c0ce7d18c4ad1b1ef49d01f6257cc
- Quelldatensatz
- uspto-grants-1999_03
- Patentnummer
- US05885979
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