2-Methyl-5-(2-nitrovinyl)furan → 2-(5-Methylfuran-2-yl)ethan-1-amine

HRID 1511606Notes

Reaction equation

HRID 1511606 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH:7]=[CH:8][N+:9]([O-])=O)=[CH:5][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[O:3][C:4]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 5380062-Methyl-5-(2-nitrovinyl)furanHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 149337782-(5-Methylfuran-2-yl)ethan-1-amineYield 107.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.0 g of 2-methyl-5-(2-nitrovinyl)furan prepared in the step 1 in 50 mL of dry THF was slowly dropped into a solution of 1.0 g of ice-cooled lithium aluminum hydride in 50 mL of dry THF. The reaction solution was gradually heated followed by heating to reflux for 4 hours. The reaction solution was cooled, ice was gradually added thereto to decompose an excess of lithium aluminum hydride and the reaction solution was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo to give 1.75 g of the objective compound as yellow liquid.

Workup

  1. temperatureThe reaction solution was gradually heated
  2. temperatureby heating
  3. temperatureto reflux for 4 hours
  4. temperatureThe reaction solution was cooled
  5. additionice was gradually added
  6. extractionthe reaction solution was subjected to extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-69c33c318c41493fa1f6f2b98565d5af
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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