Reaktion #9653

Reaktionsgleichung

methyl 4-(3′-methoxy-4′-nitro-1,1′-biphenyl-4-yl)-2,2-dimethyl -4-oxobutanoate

HCl

→

methyl 4-(4′-amino-3′-methoxy-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

Ausbeute 67.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting suspension was heated
2. 2
   Temperaturat reflux for 2.5 h
3. 3
   Filtrationfiltered through a pad of Celite®
4. 4
   workup.ADDITIONWater was added
5. 5
   Extraktionthe mixture was extracted with ethyl acetate
6. 6
   Trocknenthe combined organic phases were dried over anhydrous sodium sulfate
7. 7
   SonstigeSolvent was removed under reduced pressure
8. 8
   Sonstigethe residue was triturated with ethyl acetate/hexane

Vorschrift

To a solution of methyl 4-(3′-methoxy-4′-nitro-1,1′-biphenyl-4-yl)-2,2-dimethyl -4-oxobutanoate (670 mg, 1.80 mmol) in 85% aqueous ethanol (27 mL) was added iron powder (1.01 g, 18.04 mmol) and 2 N aqueous HCl (0.9 mL, 1.8 mmol), and the resulting suspension was heated at reflux for 2.5 h. The mixture was then cooled to rt, and filtered through a pad of Celite®. Water was added, the mixture was extracted with ethyl acetate, and the combined organic phases were dried over anhydrous sodium sulfate. Solvent was removed under reduced pressure and the residue was triturated with ethyl acetate/hexane to afford methyl 4-(4′-amino-3′-methoxy-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (410 mg, 67%). LC-MS ret. time 2.58 min, m/z 342.1 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.31 (s, 6H), 3.28 (s, 2H), 3.66 (s, 3H), 3.90 (s, 3H), 6.75 (d, 1H), 7.02–7.09 (m, 2H), 7.59 (d, 2H), 7.94 (d, 2H).

Quelle