Water → N-[3-(5-isopropyl-4-methoxy-2-methylbenzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide

HRID 24382

Reaktionsgleichung

Reaktionsgleichung von HRID 24382
[CH:1]([C:4]1[C:5]([O:13][CH3:14])=[CH:6][C:7]([CH3:12])=[C:8]([CH:11]=1)[CH:9]=O)([CH3:3])[CH3:2].[C:15]([NH:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][C:24](=[O:28])[NH:25]2)=[CH:21][CH:20]=1)(=[O:17])[CH3:16].N1CCCC1.O>C(O)C>[CH:1]([C:4]1[C:5]([O:13][CH3:14])=[CH:6][C:7]([CH3:12])=[C:8]([CH:11]=1)[CH:9]=[C:23]1[C:22]2[C:26](=[CH:27][C:19]([NH:18][C:15](=[O:17])[CH3:16])=[CH:20][CH:21]=2)[NH:25][C:24]1=[O:28])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 31268PyrrolidineHCID 2749839N-(2-Oxoindolin-6-yl)acetamideHCID 32761295-Isopropyl-4-methoxy-2-methylbenzaldehyde

Produkt 1

HCID 57270199N-[3-(5-isopropyl-4-methoxy-2-methylbenzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 5-isopropyl-4-methoxy-2-methylbenzaldehyde (0.25 g, 1.3 mmol), 6-acetamido-2-oxindole (0.25 g, 1.3 mmol) and pyrrolidine (0.54 ml, 6.5 mmol) in ethanol (4 ml) was held in a sealed tube at 100° C. for 12 hours. The reaction was cooled and then poured into water (100 ml). The solid which formed was removed by filtration, washed with water and then dissolved in ethyl acetate (200 ml). The ethyl acetate solution was dried over magnesium sulfate and concentrated. The resulting solid was triturated with dichloromethane/hexanes to afford 0.33 g (70%) of N-[3-(5-isopropyl-4-methoxy-2-methylbenzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide as a brownish yellow solid.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customThe solid which formed
  3. customwas removed by filtration
  4. washwashed with water
  5. dissolutiondissolved in ethyl acetate (200 ml)
  6. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe resulting solid was triturated with dichloromethane/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e98db52dd1d24397b55062fec6a0fdab
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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