3-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester → Methyl 4-aminothiophene-3-carboxylate Hydrochloride

HRID 231646

Reaktionsgleichung

Reaktionsgleichung von HRID 231646
O=[C:2]1[CH:6]([C:7]([O:9][CH3:10])=[O:8])[CH2:5][S:4][CH2:3]1.[ClH:11].[NH2:12]O>CO>[ClH:11].[NH2:12][C:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][S:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl esterHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 2777609Methyl 4-aminothiophene-3-carboxylate HydrochlorideAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-Oxo-4-methoxycarbonyltetrahydrothiophene (28 g) was heated under reflux for 1 hour with hydroxylamine hydrochloride (11.5 g) in methanol (80 ml). The mixture was then cooled and a first crop was filtered off and washed with dry diethyl ether to afford the title compound (18.4 g, 57.6%) m.p. 203° to 205° C. On further cooling a second crop (2.7 g, 8.5%) was obtained, m.p. 201° to 202° C. The total yield was thus 66.1%.

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. filtrationa first crop was filtered off
  3. washwashed with dry diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-bfaff0b14b7248de9e161e3a59afa063
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04847386

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