Sodium Hydroxide → 3-Amino-1-(3-chlorophenyl)propan-1-ol

HRID 1186517

Reaktionsgleichung

Reaktionsgleichung von HRID 1186517
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([C:14](=[O:18])[CH2:15][C:16]#[N:17])[CH:11]=[CH:12][CH:13]=1.[OH-].[Na+]>C1COCC1>[NH2:17][CH2:16][CH2:15][CH:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=1)[OH:18]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 1408553-(3-Chlorophenyl)-3-oxopropanenitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 649831703-Amino-1-(3-chlorophenyl)propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred suspension of LAH (16 g, 90 mmol) in dry THF (200 mL) was added a solution of 3-(3-chlorophenyl)-3-oxopropanenitrile (10.4 g, 270 mmol) in dry THF (200 mL) dropwise at 0° C. under nitrogen atmosphere. The mixture was warmed to 25° C. and then heated at 60° C. for 3 hours. After cooling to 0° C., a saturated solution of sodium hydroxide was added dropwise and extracted with ethyl acetate (200 mL). The solution was dried over anhydrous sodium sulfate and concentrated to dryness. The crude 3-amino-1-(3-chloro-phenyl)-propan-1-ol obtained was used in the next step without further purification. (Yield 14.5 g). LC-MS: [M+H]+ 186.

Aufarbeitung

  1. temperatureheated at 60° C. for 3 hours
  2. temperatureAfter cooling to 0° C.
  3. extractionextracted with ethyl acetate (200 mL)
  4. dry with materialThe solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-cb16a1db88aa4de597a505428615ce3f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

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