Реакция #1885007

Уравнение реакции

tin chloride

4-n-butylaniline

Sodium nitrite

→

solid

Выход 66.0%

p-Butylphenylhydrazine

Выход 66.0%

Растворители

hydrochloric acid

hydrochloric acid

water

Условия реакции

Обработка

1. 1
   Температураcooled
2. 2
   workup.ADDITIONwas added slowly
3. 3
   workup.STIRRINGthe resulting suspension was stirred at 0° C. for 3 h
4. 4
   ФильтрацияThe solid was filtered
5. 5
   workup.DISSOLUTIONdissolved in a mixture of 40% potassium hydroxide solution (200 mL) and ethyl acetate (200 mL)
6. 6
   ДругоеThe organic layer was separated
7. 7
   Экстракцияthe aqueous layer was further extracted with ethyl acetate
8. 8
   ПромывкаThe combined organic extracts were washed with 10% hydrochloric acid (120 mL)
9. 9
   Фильтрацияthe solid was filtered
10. 10
    ДругоеThe organic layer was separated
11. 11
    Сушкаdried over Na2SO4
12. 12
    Другоеthe solvent was evaporated
13. 13
    ДругоеThe resulting solid was recrystallized from ethanol

Методика

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).

Источник