Methyl 5-nitro-2-furoate → Methyl 5-aminofuran-2-carboxylate

HRID 1668294Notes

Reaction equation

HRID 1668294 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[O:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 94882Methyl 5-nitro-2-furoateHCID 178418361HCID 178418361, compound

Product 1

HCID 5072225Methyl 5-aminofuran-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 100 mg of methyl 5-nitro-2-furoate (Lancaster Synthesis, Windham, N.H., USA) in 20 ml of EtOAc was stirred with 20 mg of Pd/C (10%) under one atmospheric pressure of hydrogen gas. After at RT for 2 hours, the mixture was filtered through a celite pad and concentrated. Pure methyl 5-amino-2-furoate was obtained by purification on a fresh silica gel column eluted with 30% EtOAc in hexane.

Workup

  1. filtrationthe mixture was filtered through a celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-206b835d1a824cd7b5c7bc3d9f27e931
Source dataset
uspto-grants-2011_08
Patent number
US07989434B2

Reaction notes

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