Hydrochloric Acid → Ethyl 5-aminothiophene-2-carboxylate

HRID 850964

Reaktionsgleichung

Reaktionsgleichung von HRID 850964
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([N+:11]([O-])=O)=[CH:9][CH:10]=1)=[O:5])[CH3:2].Cl.[Sn].[OH-].[Na+]>C(Cl)Cl>[NH2:11][C:8]1[S:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 304627Ethyl 5-nitrothiophene-2-carboxylateHCID 5352426Tin atom

Produkt 1

HCID 21585769Ethyl 5-aminothiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 60.4 g. of ethyl-5-nitro-2-thiophenecarboxylate and 480 ml. of concentrated hydrochloric acid is cooled in an ice-bath to below -5°. To this mixture is added 72 g. of granular tin in small amounts, keeping the temperature near -5°. After stirring for 6 hours, 575 ml. of 10 N sodium hydroxide is added to neutralize the mixture. Methylene chloride and Celite are added and the mixture is filtered. The methylene chloride layer of the filtrate is separated, dried over sodium sulfate, and filtered through Magnesol. Evaporation affords an oil which is distilled to yield the product.

Aufarbeitung

  1. additionA mixture of 60.4 g
  2. additionTo this mixture is added 72 g
  3. customnear -5°
  4. filtrationthe mixture is filtered
  5. customThe methylene chloride layer of the filtrate is separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered through Magnesol
  8. customEvaporation
  9. customaffords an oil which
  10. distillationis distilled
  11. customto yield the product

Quellen und Nachweise

ORD-Eintrag
ord-7258dbe31670400d8f4a7c2bd8507fcb
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04382143

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