Acetic Acid → HCID 58358306, Verbindung

HRID 446766

Reaktionsgleichung

Reaktionsgleichung von HRID 446766
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:15][CH:14]3[C:16]([NH:18][NH2:19])=[O:17])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:20]1[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([CH:30]=O)[C:24]=2[CH:23]=[CH:22][N:21]=1.C(O)(=O)C>C(O)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH:13]3[CH2:15][CH:14]3[C:16]([NH:18]/[N:19]=[CH:30]/[C:25]3[CH:26]=[CH:27][CH:28]=[C:29]4[C:24]=3[CH:23]=[CH:22][N:21]=[CH:20]4)=[O:17])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 7016853Isoquinoline-5-carboxaldehydeHCID 583583052-(4-Cyclohexylphenyl)cyclopropanecarbohydrazide

Produkt 1

HCID 58358306HCID 58358306, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a room temperature solution of 2-(4-cyclohexylphenyl)cyclopropanecarbohydrazide (200 mg) in ethanol (20 mL), was added isoquinoline-5-carbaldehyde (122 mg, 0.77 mmol) and acetic acid (0.5 mL). The reaction mixture was then heated at 80° C. for 3 h, concentrated in vacuo and the residue diluted with water and extracted with EtOAc (2×20 mL). The layers were separated and then the combined organic layers were washed with a saturated NaHCO3 solution, dried over magnesium sulfate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via column chromatography eluting with 2% MeOH in dichloromethane to afford (E)-2-(4-cyclohexylphenyl)-N′-(isoquinolin-5-ylmethylene)cyclopropanecarbohydrazide (100 mg, 33%) as a white solid.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionthe residue diluted with water
  3. extractionextracted with EtOAc (2×20 mL)
  4. customThe layers were separated
  5. washthe combined organic layers were washed with a saturated NaHCO3 solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto obtain the crude product
  10. customThe crude material was purified via column chromatography
  11. washeluting with 2% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-30f36dbb74014371aea12e360eb5eb25
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481532B2

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