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Hydrochloric Acid → (E)-3-[6-[[3,5-Bis(trimethylsilyl)benzoyl]amino]-pyridin-3-yl]acrylic acid

HRID 2265084
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2265084
[CH3:1][Si:2]([CH3:30])([CH3:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]CC)=[O:18])=[CH:11][CH:10]=1)=[O:7].[OH-].[Na+].Cl>C(O)C>[CH3:30][Si:2]([CH3:1])([CH3:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86644273(E)-Ethyl 3-[6-[[3,5-bis(trimethylsilyl)benzoyl]amino]pyridin-3-yl]acrylate

Produkt 1

HCID 59446288(E)-3-[6-[[3,5-Bis(trimethylsilyl)benzoyl]amino]-pyridin-3-yl]acrylic acidAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

Compound 1b (232 mg) was dissolved in ethanol (7.89 ml). A 2N sodium hydroxide aqueous solution (5.26 ml) was added thereto and the mixture was stirred at room temperature overnight. The reaction mixture was ice-cooled, and a 2N hydrochloric acid aqueous solution (5.26 ml) was added to neutralize the mixture. Then the solvent was distilled off. The reaction mixture was ice-cooled, and a 2N hydrochloric acid aqueous solution (0.5 ml) was added to adjust the pH of the mixture to 1. The mixture was stirred for 1 hour. The precipitated solid was filtered off and vacuum-dried to give Compound 1 (88.0 mg, 41%) as a white solid.

Aufarbeitung

  1. temperaturecooled
  2. distillationThen the solvent was distilled off
  3. temperaturecooled
  4. additiona 2N hydrochloric acid aqueous solution (0.5 ml) was added
  5. stirringThe mixture was stirred for 1 hour
  6. filtrationThe precipitated solid was filtered off
  7. customvacuum-dried

Quellen und Nachweise

ORD-Eintrag
ord-be65e00901654df79e4a3324fcca969c
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07855300B2

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