Ethanol → 4-(5-Cyclopropyl-2-isoxazolin-3-yl)pyridine

HRID 1076692

Reaktionsgleichung

Reaktionsgleichung von HRID 1076692
C(Cl)(=O)C1C=C[N:5]=[CH:4][CH:3]=1.[CH:10]([CH:12]1[CH2:14][CH2:13]1)=[CH2:11].C([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])C.C([OH:24])C>>[CH:12]1([CH:10]2[O:24][N:5]=[C:4]([C:3]3[CH:19]=[CH:18][N:17]=[CH:20][CH:21]=3)[CH2:11]2)[CH2:14][CH2:13]1

Komponenten

5

Edukt 4

HCID 702Ethanol2×HCID 8471TriethylamineHCID 136498EthenylcyclopropaneHCID 417436Pyridine-4-carbonyl chloride

Produkt 1

HCID 215378854-(5-Cyclopropyl-2-isoxazolin-3-yl)pyridine

Versuchsvorschrift

To a stirred mixture containing 3.8 g. of isonicotinoyl chloride, oxime hydrochloride and 1.4 g. of vinylcyclopropane in 100 ml. of ethanol is added dropwise over a 1 hour period, a solution 4.1 g. of triethylamine in 40 ml. of ethanol. The reaction is stirred for 1 hour and then the solvent is removed under reduced pressure. The residue is extracted with ether and the ether solution is dried over sodium sulfate. The solution is filtered and then the solvent is removed giving a yellow solid. The solid is recrystallized from ethanol giving white crystals, melting point 102°-108°C.

Aufarbeitung

  1. additionTo a stirred mixture containing 3.8 g
  2. customthe solvent is removed under reduced pressure
  3. extractionThe residue is extracted with ether
  4. dry with materialthe ether solution is dried over sodium sulfate
  5. filtrationThe solution is filtered
  6. customthe solvent is removed
  7. customgiving a yellow solid
  8. customThe solid is recrystallized from ethanol giving white crystals, melting point 102°-108°C.

Quellen und Nachweise

ORD-Eintrag
ord-9d0a7d514cfc41bdb84fbc60e815f3de
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03957805

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