Acetic Acid → HCID 54094934, Verbindung

HRID 35683

Reaktionsgleichung

Reaktionsgleichung von HRID 35683
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7][C:6](=[CH:16][N:17](C)C)[C:5]2=[O:20].C(O)(=O)C.[C:25]([O:29][C:30]([N:32]([CH3:34])N)=[O:31])([CH3:28])([CH3:27])[CH3:26]>CO.O1CCCC1>[C:25]([O:29][C:30]([N:32]([CH3:34])[NH:17][CH:16]=[C:6]1[C:5](=[O:20])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 37482801-Boc-1-methylhydrazineHCID 54453990HCID 54453990, Verbindung

Produkt 1

HCID 54094934HCID 54094934, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 6-chloro-3-dimethylaninometylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.00 g) 1-tert-butoxycarbonyl-1-meth-ylhydrazine (1.50 g) and acetic acid (1.20 ml) in methanol (100 ml) and tetrahydrofuran (100 ml) was refluxed for 9 hours with stirring. 1-tert-Butoxycarbonyl-1-methylhydrazine (1.50 g) was added to the mixture and the stirring was continued for 8 hours at reflux conditions. After the solvent was evaporated in vacuo, saturated aqueous sodium hydrogen carbonate (15 ml) was added to the mixture and extracted with ethyl acetate (30 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue (3.90 g) was chromatographed on silica gel by eluting with chloroform to give 3-(2-tert-butoxycarbonyl-2-methylhydrazino)methylene-6-chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.10 g) as yellow amorphous.

Aufarbeitung

  1. temperatureat reflux conditions
  2. customAfter the solvent was evaporated in vacuo, saturated aqueous sodium hydrogen carbonate (15 ml)
  3. additionwas added to the mixture
  4. extractionextracted with ethyl acetate (30 ml)
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue (3.90 g) was chromatographed on silica gel
  9. washby eluting with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-c48d16fc29f746318e3d664348d4c514
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767780

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