Ethyl 5-nitro-2-furoate → 2-furancarboxylic acid, 5-amino-, ethyl ester

HRID 850969Notes

Reaction equation

HRID 850969 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[O:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 70341Ethyl 5-nitro-2-furoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 1674842-furancarboxylic acid, 5-amino-, ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 53.3 g. of ethyl 5-nitro-2-furancarboxylate, 5 g. of 10% palladium on carbon, and 250 ml. of absolute ethanol is shaken in an atmosphere of hydrogen until no more hydrogen is taken up. The catalyst is filtered and the filtrate evaporated. The thick oily residue is dissolved in a small amount of methylene chloride and the solution is filtered through Magnesol. The solvent is evaporated to yield the product.

Workup

  1. additionA mixture of 53.3 g
  2. filtrationThe catalyst is filtered
  3. customthe filtrate evaporated
  4. dissolutionThe thick oily residue is dissolved in a small amount of methylene chloride
  5. filtrationthe solution is filtered through Magnesol
  6. customThe solvent is evaporated
  7. customto yield the product

Sources & evidence

ORD record
ord-bf758e6d689c42e8a7906e3779a331a8
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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