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

HRID 14245Notes

Reaction equation

HRID 14245 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>C(O)C.[Pd]>[NH2:1][C:4]1[O:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 94882Methyl 5-nitro-2-furoate

Product 1

HCID 5072225Methyl 5-aminofuran-2-carboxylateYield 52.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 5-nitro-2-furoate (13 g, 76 mmol) and 10% Pd/C (1.3 g) in ethanol (150 mL) was shaken under an atmosphere of hydrogen at 40 psi for 18 h. The reaction mixture was filtered through diatomaceous earth and concentrated under reduced pressure to afford a crude oil. Purification by flash column chromatography (silica, 1:1 hexanes/ethyl acetate) provided methyl 5-amino-2-furoate (5.6 g): 1H NMR (500 MHz, CDCl3) δ 7.11-7.10 (m, 1H), 5.31-5.29 (m, 1H), 4.31 (br s, 2H), 3.84 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure
  3. customto afford a crude oil
  4. customPurification by flash column chromatography (silica, 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-3f265dd9e5684da88ca5ec6201f91dfb
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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