反応 #1595971

反応方程式

methyl 4-(4-aminophenyl)butanoate

ammonium chloride

NH3

→

title compound

収率 35.1%

4-(4-aminophenyl)butanamide

収率 35.1%

溶媒

methanol

反応条件

後処理

1. 1
   その他The vial was sealed
2. 2
   その他After this time, the crude reaction solution
3. 3
   濃縮was concentrated under reduced pressure
4. 4
   その他The residue was absorbed on silica (10 g)
5. 5
   その他then purified by chromatography on silica

実験手順

A 100-mL vial was charged with methyl 4-(4-aminophenyl)butanoate (2.07 g, 10.7 mmol), ammonium chloride (0.76 g, 14.2 mmol) in methanol (10 mL). To this mixture was added NH3 (10 mL, 7N in methanol, 70.0 mmol, 6.5 eq.). The vial was sealed and the resulting mixture was stirred at 100° C. for 20 h. After this time, the crude reaction solution was concentrated under reduced pressure. The residue was absorbed on silica (10 g) then purified by chromatography on silica using dichloromethane/methanol (10:0 to 9:1) as eluent to afford the title compound (0.67 g, 35%) as a white solid. MW=178.23. 1H NMR (DMSO-d6, 500 MHz) δ 7.20 (br s, 1H), 6.83-6.80 (m, 2H), 6.66 (br s, 1H), 6.49-6.46 (m, 2H), 2.37 (t, J=7.5 Hz, 2H), 2.01 (t, J=7.5 Hz, 2H), 1.68 (quin, J=7.5 Hz, 2H).

出典