6-(4-Nitrophenoxy)-hexanoic acid methyl ester → 6-(4-Aminophenoxy)-hexanoic acid methyl ester

HRID 83789

Reaktionsgleichung

Reaktionsgleichung von HRID 83789
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1>CN(C)C=O.[Ni]>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1

Komponenten

4

Edukt 1

HCID 146502956-(4-Nitrophenoxy)-hexanoic acid methyl ester

Produkt 1

HCID 146502966-(4-Aminophenoxy)-hexanoic acid methyl esterAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Method-A Through a mixture of 6-(4-aminophenoxy)-hexanoic acid hydrochloride 16 (150 g, 578 mmol) in methanol (3 L) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 48 hours. Methanol (1.5 L) was distilled off, ice water (1 L) was added and the pH adjusted to 7.5 with K2CO3. Crude 17 was extracted into chloroform, washed with 5% NaHCO3 solution, then water, and then dried over Na2SO4 and distilled to give 17 (60 g, 43.8%) as a thick brown syrup. Method-B 6-(4-Nitrophenoxy)-hexanoic acid methyl ester 21 (40 g, 149.81 mmol) was dissolved in dimethyl formamide (200 ml) in a pressure vessel. Raney nickel (20 g) was added and the mixture stirred under an atmosphere of hydrogen (4 kg) for 16 hours. Catalyst was removed by filtration and dimethyl formamide distilled off under vacuum. Crude 17 was purified by column chromatography on silica gel using chloroform as eluant to get pure 17 (28 grams, 78.8%) as a thick brown syrup.

Aufarbeitung

  1. customCatalyst was removed by filtration and dimethyl formamide
  2. distillationdistilled off under vacuum
  3. customCrude 17 was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-68d8e3382d704997bd548e91ad074dec
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846845B2

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