Реакция #219199

Уравнение реакции

3-ethoxy-4-hydroxy-5-nitrobenzaldehyde

formula 2

3-ethoxy-4-hydroxy-5-nitrobenzaldehyde

N,N-diethylaminocyanoacetamide

acetic acid

piperidine

→

N,N-diethyl-2-cyano-3-(-3-ethoxy-4-hydroxy-5-nitrophenyl)acrylamide

Выход 172.7%

Растворители

water

toluene

Условия реакции

Обработка

1. 1
   Концентрированиеthe reaction mixture was concentrated to a volume of 20-30 mL
2. 2
   Другоеquenched into dilute hydrochloric acid
3. 3
   Температураchilled water (200 mL)
4. 4
   ФильтрацияThe precipitated solid was filtered
5. 5
   Другоеdried

Методика

A flask was charged with 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (20 g, 0.0947 mole) (formula 2 where R is ethyl) and N,N-diethylaminocyanoacetamide (formula (3)) (14.6 g, 0.1042 mol), acetic acid (3.13 g), and piperidine (4.45 g), along with toluene (200 mL), and was heated to a reflux temperature of about 100-115° C. with continuous removal of water azeotrophically for about 15 hours. After the reaction was complete, the reaction mixture was concentrated to a volume of 20-30 mL, quenched into dilute hydrochloric acid and chilled water (200 mL), and stirred for 60 minutes. The precipitated solid was filtered and dried to provide 30 g (95% yield, HPLC purity of 94% (including isomer)) of N,N-diethyl-2-cyano-3-(-3-ethoxy-4-hydroxy-5-nitrophenyl)acrylamide. The product was used as such directly to the next stage. MR=110.0-117.2° C.

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