Pyridine → Methyl 5-formyl-2-thiophenecarboxylate oxime

HRID 1463487

Reaktionsgleichung

Reaktionsgleichung von HRID 1463487
[CH:1]([C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=O)=[CH:5][CH:4]=1)=[O:2].Cl.[NH2:13][OH:14].N1C=CC=CC=1>C(O)C>[CH:1]([C:3]1[S:7][C:6]([C:8](=[N:13][OH:14])[O:10][CH3:11])=[CH:5][CH:4]=1)=[O:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 818924Methyl 5-formylthiophene-2-carboxylate

Produkt 1

HCID 86745040Methyl 5-formyl-2-thiophenecarboxylate oximeAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of methyl 5-formyl-2-thiophenecarboxylate, prepared according to Example 10, (6.26 g, 36.78 mmoles), hydroxylamine hydrochloride (3.07 g, 44.14 mmoles) and pyridine (3.49 g, 44.14 mmoles) in 200 ml of ethanol was refluxed for 2 hours. The ethanol was removed in vacuo, the residue dissolved in ether and washed with water. The organic layer was dried (magnesium sulfate) and evaporated to a yellow solid. Trituration with a small amount of ether furnished the title compound as a white solid (4.93 g, 72%), m.p. 164°-7° C. Oxime Z:E ratio:(82:18).

Aufarbeitung

  1. temperaturewas refluxed for 2 hours
  2. customThe ethanol was removed in vacuo
  3. dissolutionthe residue dissolved in ether
  4. washwashed with water
  5. dry with materialThe organic layer was dried (magnesium sulfate)
  6. customevaporated to a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-7664b9f1a3314becacdfac834dcf8ff4
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300655

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