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Hydrazine → HCID 66615831, Verbindung

HRID 76072
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 76072
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2].O.[C:23]([OH:27])(=O)[CH:24]=O.[OH-].[NH4+:29].[NH2:30]N>O.C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:24][C:23](=[O:27])[NH:30][N:29]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 9321HydrazineHCID 14923Ammonium HydroxideHCID 15620607Glyoxylic acid, monohydrateHCID 66615847[4-(4-Acetyl-phenyl)-cyclohexyl]-acetic acid ethyl ester

Produkt 1

HCID 66615831HCID 66615831, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of [4-(4-acetyl-phenyl)-cyclohexyl]-acetic acid ethyl ester (17 g, 59 mmol, 1.0 equiv) in 100 Ml glacial acetic acid was added glyoxylic acid monohydrate (5.4 g, 59 mmol, 1.0 equiv) as a solid. The solution was heated to 100° C. for 2 h. The mixture was then cooled to 40° C., then 75 Ml water was added followed by 120 Ml of a 28% ammonium hydroxide solution until the Ph was measured to be 8. Hydrazine (2.0 Ml, 65 mmol, 1.1 equiv) was then added via syringe, and the reaction was then heated to 95° C. for 2 hr. Upon cooling to room temperature, a solid precipitate was filtered off to afford the title compound in addition to the uneliminated product {4-[4-(5-hydroxy-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-cyclohexyl}-acetic acid ethyl ester. This mixture was taken into the next step without further purification. (M+H)+341.2.

Aufarbeitung

  1. temperatureThe mixture was then cooled to 40° C.
  2. temperaturethe reaction was then heated to 95° C. for 2 hr
  3. temperatureUpon cooling to room temperature
  4. filtrationa solid precipitate was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-adf7c16b46704be0b95324c838934bb7
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08835451B2

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