Water → (2-Aminopyridin-3-yl)methanol

HRID 8948

Reaktionsgleichung

Reaktionsgleichung von HRID 8948
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[NH2:11])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[NH2:11][C:6]1[C:5]([CH2:4][OH:3])=[CH:10][CH:9]=[CH:8][N:7]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12433260Ethyl 2-aminopyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 11159325(2-Aminopyridin-3-yl)methanolAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-aminonicotinic acid ethyl ester (1.74 g, 10.5 mmol) in anhydrous THF (35 mL) was added a solution of lithium aluminum hydride (0.60 g, 15.7 mmol) in THF (17 mL) at 0° C. over 15 min and the mixture stirred for 1.5 h. To the reaction was added sequentially 0.6 mL H2O, 0.6 mL 15% aqueous NaOH and 1.8 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 2-amino-3-hydroxymethylpyridine (1.03 g, 79%) as a yellow crystalline solid. 1H NMR (CDCl3) δ 3.14 (br s, 1H (OH)), 4.60 (s, 2H), 5.00 (br s, 1H (NH)), 6.59 (t, 1H, J=6.0 Hz), 7.28 (d, 1H, J=7.5 Hz), 7.94 (d, 1H, J=7.5 Hz).

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-075f816db41f43d982f69b4ea63db836
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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