Реакция #11446

Уравнение реакции

tert-butyl 4-aminobutylcarbamate

2,4-dichloro-6-methyl-3-nitropyridine

→

tert-butyl 4-[(2-chloro-6-methyl-3-nitropyridin-4-yl)amino]butylcarbamate

Выход 98.5%

Растворители

N,N-dimethylformamide

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was removed by vacuum distillation
2. 2
   workup.DISTILLATIONa 24/40 short path distillation head
3. 3
   Температураwarm water
4. 4
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (700 mL)
5. 5
   Промывкаwashed with water (3×100 mL)
6. 6
   Сушкаdried over magnesium sulfate
7. 7
   Концентрированиеconcentrated under reduced pressure
8. 8
   ДругоеThe crude product was purified by column chromatography (50×450 mm silica gel eluting with 1:1 hexane:ethyl acetate)

Методика

A solution of tert-butyl 4-aminobutylcarbamate (32.12 g, 170.6 mmol) in N,N-dimethylformamide (200 mL) was added over a period of 90 minutes to a solution of 2,4-dichloro-6-methyl-3-nitropyridine (35.09 g, 169.5 mmol) in N,N-dimethylformamide (500 mL). The reaction mixture was stirred at ambient temperature overnight. The solvent was removed by vacuum distillation using a 24/40 short path distillation head and warm water. The residue was dissolved in ethyl acetate (700 mL), washed with water (3×100 mL), dried over magnesium sulfate and then concentrated under reduced pressure. The crude product was purified by column chromatography (50×450 mm silica gel eluting with 1:1 hexane:ethyl acetate) to provide 59.90 g of tert-butyl 4-[(2-chloro-6-methyl-3-nitropyridin-4-yl)amino]butylcarbamate.

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