Ammonia → 7-Ethoxy-5,8-dihydronaphthalen-1-amine

HRID 30530

Reaktionsgleichung

Reaktionsgleichung von HRID 30530
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[NH2:14])=[CH:6][CH:5]=1)[CH3:2].C(O)(C)(C)C.[Li].N>O1CCCC1.O.CO>[CH2:1]([O:3][C:4]1[CH2:13][C:12]2[C:11]([NH2:14])=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH:5]=1)[CH3:2]

Komponenten

8

Edukt 4

HCID 222AmmoniaHCID 6386tert-ButanolHCID 3028194LithiumHCID 450914037-Ethoxynaphthalen-1-amine

Produkt 1

HCID 230669967-Ethoxy-5,8-dihydronaphthalen-1-amineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Next, to a flask containing a mixture of 7-ethoxy-naphthalen-1-ylamine (1.80 g, 9.61 mmol) and t-butanol (2.13 g, 28.8 mmol) in tetrahydrofuran (20 mL) was collected liquid ammonia (300 mL) at −78° C. To the mixture was added lithium (0.200 g, 28.8 mmol) over 30 minutes and stirred at −78° C. for 1 hour. Methanol and water was added, and the mixture was stirred at room temperature for 16 hours to allow ammonia to evaporate. To the obtained residue was added ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 7-ethoxy-5,8-dihydronaphthalen-1-ylamine (1.37 g, 76% yield).

Aufarbeitung

  1. additionNext, to a flask containing
  2. customwas collected liquid ammonia (300 mL) at −78° C
  3. stirringthe mixture was stirred at room temperature for 16 hours
  4. customto evaporate
  5. additionTo the obtained residue was added ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e8fa031bb0b149fca7ae542ca3797309
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423175B2

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