Acetic Anhydride → Alpha-acetamido-6-methylindole-3-acrylic acid ethylester

HRID 616270

Reaktionsgleichung

Reaktionsgleichung von HRID 616270
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:13]([O:15][C:16](=[O:25])[CH:17]([NH:21][C:22](=[O:24])[CH3:23])C(O)=O)[CH3:14].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[CH2:13]([O:15][C:16](=[O:25])[C:17]([NH:21][C:22](=[O:24])[CH3:23])=[CH:11][C:6]1[C:5]2[C:9](=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1)[CH3:14]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 32762552-Acetamido-3-ethoxy-3-oxopropanoic acid2×HCID 47779026-Methylindole-3-carboxaldehyde

Produkt 1

HCID 54175825Alpha-acetamido-6-methylindole-3-acrylic acid ethylesterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A 3-l. three-necked flask, equipped with a mechanical stirrer, a thermometer and a dropping funnel with pressure-equalizing arm was charged with 100 g (0.63 mol) of 6-methylindole-3-carboxaldehyde, 119 g (0.63 mol) of acetamidomalonic acid monoethylester and 500 ml of pyridine. The mixture was stirred and kept at 15° with a cold water bath while 175 ml of acetic anhydride was added over 15 minutes. The yellow solution was stirred at room temperature for 3 hours. Then an additional portion of 36 g (0.19 mol) of acetamidomalonic acid monoethyl ester was added and stirring at room temperature was continued for 22 hours before 1 kg of ice was added. The temperature fell to -10° and the product began to precipitate. The suspension was stirred at room temperature for 5 hours and poured into 2 1 of water. After 20 minutes, the precipitate was collected by suction filtration, washed with water and dried at 50° in an air oven overnight to afford 159.5 g (89%) of crude product as yellow crystals, m.p. 159°-162° (sinters at 75°).

Aufarbeitung

  1. customthree-necked flask, equipped with a mechanical stirrer
  2. additionwas added over 15 minutes
  3. stirringThe yellow solution was stirred at room temperature for 3 hours
  4. stirringstirring at room temperature
  5. additionwas added
  6. customfell to -10°
  7. customto precipitate
  8. stirringThe suspension was stirred at room temperature for 5 hours
  9. additionpoured into 2 1 of water
  10. filtrationthe precipitate was collected by suction filtration
  11. washwashed with water
  12. customdried at 50° in an air oven overnight

Quellen und Nachweise

ORD-Eintrag
ord-e133900a9c3641189a1bfb2f1c91b88c
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04073795

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