Реакция #1135830

ord-e6a044578442493aa7132664e56ccc35

Уравнение реакции

COC(=O)CCCCCCC(=O)Nc1ccc(Br)cc1[N+](=O)[O-]
methyl 8-(4-bromo-2-nitrophenylamino)-8-oxooctanoate
O.[Cl][Sn][Cl]
SnCl2.H2O
COC(=O)CCCCCCC(=O)Nc1ccc(Br)cc1N
methyl 8-(2-amino-4-bromophenylamino)-8-oxooctanoate
Выход 66.9%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ТемператураThe reaction was heated
  2. 2
    Температураto reflux overnight
  3. 3
    Другоеquenched by water
  4. 4
    ФильтрацияThe mixture was filtered
  5. 5
    Экстракцияthe filtrate was extracted with ethyl acetate
  6. 6
    ДругоеThe combined organic layer was dried
  7. 7
    Концентрированиеconcentrated
  8. 8
    Другоеpurified by biotage column chromatography

Методика

To a solution of methyl 8-(4-bromo-2-nitrophenylamino)-8-oxooctanoate (241 mg, 0.623 mmol) in EtOH was added SnCl2.H2O (490 mg, 2.37 mmol). The reaction was heated to reflux overnight and quenched by water. The mixture was filtered and the filtrate was extracted with ethyl acetate. The combined organic layer was dried, concentrated and purified by biotage column chromatography to afford methyl 8-(2-amino-4-bromophenylamino)-8-oxooctanoate (149 mg)

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09381196B2uspto-grants-2016_07