Ethyl 2-nitrothiophene-3-acetate → Ethyl 2-aminothiophene-3-acetate

HRID 1860248Notes

Reaction equation

HRID 1860248 reaction equation
[N+:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([O-])=O>O1CCOCC1.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[NH2:1][C:4]1[S:5][CH:6]=[CH:7][C:8]=1[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 1

HCID 67550584Ethyl 2-nitrothiophene-3-acetate

Product 1

HCID 53656999Ethyl 2-aminothiophene-3-acetateYield 90%

Reagents, catalysts & solvents 2

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-nitrothiophene-3-acetate (4 g, 18.6 mmol) was dissolved in aqueous dioxan (40 ml, 4:1 dioxan/water) and treated with reduced iron powder (3.5 g, 62.7 mmol) and iron sulfate heptahydrate (400 mg, 1.44 mmol). The reaction mixture was heated at reflux for 2 hours then filtered through celite filter-aid and washed through with diethyl ether. The organic phase was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. The organic phase was dried over magnesium sulfate and evaporated to a red/black liquid and then chromatographed on silica gel using hexane/ethyl acetate (3:1) as eluent to give 3.1 g of ethyl 2-aminothiophene-3-acetate. MS(ES): m/e 186 [M+H].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationthen filtered through celite
  4. filtrationfilter-aid
  5. washwashed through with diethyl ether
  6. washThe organic phase was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. customevaporated to a red/black liquid
  9. customchromatographed on silica gel

Sources & evidence

ORD record
ord-2ed1688ab6684bc0bcdd12fe1eda74ac
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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