Water → (3-Aminonaphthalen-2-yl)methanol

HRID 604619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604619
[NH2:1][C:2]1[C:3]([C:12](O)=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[C:3]([CH2:12][OH:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 222443-Amino-2-naphthoic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10374898(3-Aminonaphthalen-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 3-amino-2-naphthoic acid (85%, 1.17 g, 5.34 mmol) in dry THF (20 mL) was added dropwise over 30 min to a stirred solution of lithium aluminum hydride (95%, 0.53 g, 13.4 mmol) in dry THF (20 mL) at 0° C. under N2. The mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was adjusted to basic pH with 1N NaOH (20 mL). The mixture was filtered and extracted with Et2O (4×100 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford (3-amino-2-naphthyl)methanol. LCMS calc.=174.1; found=174.2 (M+1)+. 1H NMR (500 MHz, CD3OD): δ 7.66 (d, J=8.0 Hz, 1H); 7.61 (s, 1H); 7.55 (d, J=8.2 Hz, 1H); 7.30-7.27 (m, 1H); 7.18-7.14 (m, 1H); 7.08 (s, 1H); 4.74 (s, 2H).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. extractionextracted with Et2O (4×100 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-348fc64e6adf44ebbb9a5667e018867c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910592B2

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