Reaktion #940009

Reaktionsgleichung

1-(3,4-dimethoxy-1-naphthyl)-8-(4-acetamidophenyl)-octane

HCl

→

aniline

Ausbeute 75.0%

1-(3,4-Dimethoxy-1-naphthyl)-8-(4-aminophenyl)-octane

Ausbeute 75.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 23 hr
2. 2
   SonstigeThen the reaction mixture was partitioned between 75 mL of CH2Cl2 and 21 mL of 2N NaOH
3. 3
   ExtraktionThe aqueous phase was extracted with CH2Cl2 (5×40 mL)
4. 4
   Trocknendried with MgSO4
5. 5
   Sonstigeevaporated to dryness

Vorschrift

A solution of 554.6 mg (1.28 mmol) of 1-(3,4-dimethoxy-1-naphthyl)-8-(4-acetamidophenyl)-octane in 20 mL of MeOH was mixed with 21 mL of 2N HCl. The reaction mixture was refluxed for 23 hr. Then the reaction mixture was partitioned between 75 mL of CH2Cl2 and 21 mL of 2N NaOH. The aqueous phase was extracted with CH2Cl2 (5×40 mL). The CH2Cl2 extracts were combined, dried with MgSO4, and evaporated to dryness. Column chromatography on silica gel with 1% MeOH in CH2Cl2 gave 374.6 mg (75%) of aniline 37: 1H NMR (250 MHz, CDCl3, TMS) δ 8.14 (d, J=8 Hz, 1H), 7.94 (d, J=8 Hz, 1H), 7.47 (t, J=8 Hz, 1H), 7.37 (t, J=8 Hz, 1H), 7.12 (s, 1H), 6.96 (d, J=8 Hz, 2H), 6.62 (d, J=8 Hz, 2H), 3.99 (s, 3H), 3.97 (s, 3H), 3.1-3.0 (m, 2H), 2.5-2.4 (m, 2H), 1.8-1.3 (m 12H).

Quelle