Hydrochloric Acid → Ethyl 5-aminothiophene-2-carboxylate

HRID 850964Notes

Reaction equation

HRID 850964 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 21585769Ethyl 5-aminothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7258dbe31670400d8f4a7c2bd8507fcb
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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