Reaktion #994841

Reaktionsgleichung

methyl 4-[4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate

hydrochloric acid

→

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

Ausbeute 95.4%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution
2. 2
   workup.ADDITIONwas slowly added until pH >8.0
3. 3
   ExtraktionThe aqueous layer was then extracted with methylene chloride (2×25 mL)
4. 4
   Trocknenthe combined organic layer was dried over sodium sulfate
5. 5
   EinengenThe mixture was concentrated under reduced pressure

Vorschrift

To a suspension of methyl 4-[4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate (2.40 g, 7.07 mmol) in 20 mL methanol, was added 7 mL concentrated hydrochloric acid at below rt. The reaction mixture was stirred at rt overnight. The mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution was slowly added until pH >8.0. The aqueous layer was then extracted with methylene chloride (2×25 mL), and the combined organic layer was dried over sodium sulfate. The mixture was concentrated under reduced pressure to afford methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate as a light red solid (2.1 g, 95%). 1H NMR (CDCl3) δ 7.96 (d, J=9 Hz, 2H), 7.60 (d, J=9 Hz, 2H), 7.46 (d, J=9 Hz, 2H), 6.76 (d, J=9 Hz, 2H), 3.85 (br s, 2H), 3.69 (s, 3H), 3.32 (s, 2H), 1.35 (s, 6H); ESI-MS m/z 312.4 (MH+); HRMS m/z calcd for MH+ 312.1594, found 312.1597.

Quelle