Реакция #72704

Уравнение реакции

4-bromo aniline

NaNO2

pyrrolidine

→

compound 134

Выход 46.2%

(E)-1-((4-Bromophenyl)diazenyl)pyrrolidine

Выход 46.2%

Растворители

HCl

H2O

KOH

Условия реакции

Обработка

1. 1
   workup.ADDITIONafter the addition
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 30 min at 0-10° C
3. 3
   ФильтрацияThe resulting precipitate was then filtered
4. 4
   Другоеrecrystallized from absolute ethanol (50 mL)

Методика

To a 0° C. solution of 4-bromo aniline (133, 10 g, 58.1 mmol) in concentrated HCl (11.7 mL) was added dropwise a solution of NaNO2 (4 g, 57.9 mmol) in H2O (5 mL). The reaction was then stirred for an additional 10 min. at 0° C. after the addition. The resulting diazonium salt solution was added at once to a solution of pyrrolidine (4.54 g, 63.9 mmol) in 1M KOH (50 mL). The reaction mixture was stirred for 30 min at 0-10° C. The resulting precipitate was then filtered and recrystallized from absolute ethanol (50 mL) to give compound 134 (6.8 g, 46.2%) as light yellow crystals.

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