反応 #1885007
ord-5df328fe7cfa4ae9b7e0828bec02fd12
反応方程式
反応条件
後処理
- 1温度cooled
- 2workup.ADDITIONwas added slowly
- 3workup.STIRRINGthe resulting suspension was stirred at 0° C. for 3 h
- 4ろ過The solid was filtered
- 5workup.DISSOLUTIONdissolved in a mixture of 40% potassium hydroxide solution (200 mL) and ethyl acetate (200 mL)
- 6その他The organic layer was separated
- 7抽出the aqueous layer was further extracted with ethyl acetate
- 8洗浄The combined organic extracts were washed with 10% hydrochloric acid (120 mL)
- 9ろ過the solid was filtered
- 10その他The organic layer was separated
- 11乾燥dried over Na2SO4
- 12その他the solvent was evaporated
- 13その他The resulting solid was recrystallized from ethanol
実験手順
Sodium nitrite (11.74 g, 0.17 mol) in water (50 mL) was added over 30 min to an ice-cooled and stirred suspension of 4-n-butylaniline (24.30 g, 0.16 mol) in 6 N hydrochloric acid (190 mL). After an additional 15 min, a suspension of tin chloride dehydrate (108.3 g, 0.4 mol) in 6 N hydrochloric acid (190 mL) was added slowly, and the resulting suspension was stirred at 0° C. for 3 h. The solid was filtered and dissolved in a mixture of 40% potassium hydroxide solution (200 mL) and ethyl acetate (200 mL). The organic layer was separated and the aqueous layer was further extracted with ethyl acetate. The combined organic extracts were washed with 10% hydrochloric acid (120 mL), a solid started to develop in the organic layer. After cooled it to 0° C., the solid was filtered. The organic layer was separated, dried over Na2SO4, and the solvent was evaporated. The resulting solid was recrystallized from ethanol to afford a white solid (17.35 g, 54%). 1H NMR (300 MHz, DMSO-d6): δ 10.18 (s, 3H), 7.10 (d, 2H, J=8.4 Hz), 6.92 (d, 2H, J=8.7 Hz), 2.51 (t, 2H, J=7.5 Hz), 1.50 (pentet, 2H, J=7.5 Hz), 1.27 (sextet, 2H, J=7.8 Hz), 0.88 (t, 3H, J=7.5 Hz).