Hydrochloric Acid → 7-Ethoxynaphthalen-1-amine

HRID 30529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30529
C(OC(=O)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=2)[CH:11]=[CH:10][CH:9]=1)(C)(C)C.Cl.C(OC(C)C)(C)C>O1CCOCC1>[CH2:19]([O:18][C:15]1[CH:16]=[C:17]2[C:12]([CH:11]=[CH:10][CH:9]=[C:8]2[NH2:7])=[CH:13][CH:14]=1)[CH3:20]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 59731041tert-Butyl 7-ethoxynaphthalen-1-ylcarbamate

Produkt 1

HCID 450914037-Ethoxynaphthalen-1-amineAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

Next, to a (7-ethoxy-naphthalen-1-yl)-carbamic acid t-butyl ester (47.9 g, 167 mmol) in 100 mL anhydrous 1,4-dioxane was added 4N HCl in 1,4-dioxane (100 mL) at 0° C. The mixture was stirred at room temperature for 2 hours. Diisopropyl ether was added to the reaction mixture and the precipitate was filtered. To the obtained solid was added saturated sodium bicarbonate and the product was extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 7-ethoxy-naphthalen-1-ylamine (27.0 g, 86.3% yield).

Aufarbeitung

  1. filtrationthe precipitate was filtered
  2. additionTo the obtained solid was added saturated sodium bicarbonate
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-95c78c1e9d5346bb9b3c7c4a3a701241
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423175B2

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