Water → (6-Aminopyridin-3-yl)methanol

HRID 8946

Reaktionsgleichung

Reaktionsgleichung von HRID 8946
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[N:7][CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[NH2:11][C:8]1[N:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 235927Ethyl 6-AminonicotinateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 2794829(6-Aminopyridin-3-yl)methanolAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 6-aminonicotinic acid ethyl ester (1.18 g, 7.1 mmol) in anhydrous THF (24 mL) was added a solution of lithium aluminum hydride (0.41 g, 10.6 mmol) in THF (12 mL) at 0° C. over 10 min and the mixture stirred for 1.5 h. To the reaction was added sequentially 0.5 mL H2O, 0.5 mL 15% aqueous NaOH and 1.5 mL H2O and the resultant slurry was filtered. The filtrate was dried (MgSO4), filtered, concentrated and purified by column chromatography (10% MeOH/CH2Cl2) to give 6-amino-3-hydroxymethylpyridine (0.61 g, 69%) as colorless crystals. 1H NMR (MeOD) δ 3.31 (s, 1H (OH)), 4.43 (s, 2H), 6.58 (d, 1H, J=8.4 Hz), 7.48 (d, 1H, J=8.7 Hz), 7.85 (s, 1H).

Aufarbeitung

  1. filtrationthe resultant slurry was filtered
  2. dry with materialThe filtrate was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (10% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-6d190122b5b7460ba966849f68654cfe
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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