Tosylmethyl isocyanide → HCID 86627461, Verbindung

HRID 1969931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969931
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=[O:8])=CC=1.CC(C)([O-])C.[K+].C(O[CH2:24][CH:25]=[C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][C:27]1=[O:35])(=O)C>O1CCCC1>[O:35]=[C:27]1[C:26]2[NH:11][CH:10]=[CH:24][C:25]=2[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[NH:28]1.[CH2:26]([C:27]([O-:35])=[O:8])[CH3:34]

Komponenten

5

Edukt 3

HCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 68938981(2-Oxo-1,2-dihydro-indol-3-ylidene)-ethyl ethanoate

Produkt 1

HCID 86627461HCID 86627461, VerbindungAusbeute 91,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

18.3 g (93.6 mmol) of p-toluenesulfonylmethyl isonitrile followed by a solution of 54 mL (93.6 mmol) of a 20% solution of potassium tert-butoxide in tetrahydrofuran in 700 mL of anhydrous tetrahydrofuran are added to a solution of 20.3 g (93.6 mmol) of (2-oxo-1,2-dihydro-indol-3-ylidene)-ethyl ethanoate dissolved in 340 mL of anhydrous tetrahydrofuran (time of addition 90 minutes). The reaction mixture is refluxed for 1 hour then the solid is filtered. The filtrate is poured into a mixture of ice and water (about 1 L) and the solution is acidified with acetic acid until the pH is 4. The solvents are concentrated by evaporation under vacuum then the solid is filtered and then recrystallized from acetic acid to give 11.05 g (37%) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate cocrystallized with one equivalent of acetic acid in the form of a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. filtrationthe solid is filtered
  3. additionThe filtrate is poured into a mixture of ice and water (about 1 L)
  4. concentrationThe solvents are concentrated by evaporation under vacuum
  5. filtrationthe solid is filtered
  6. customrecrystallized from acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-7cb282b2e2cb40efab29649e18f03d3c
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426437B2

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