4-Nitrobenzaldehyde → 4-Aminobenzaldehyde

HRID 539944Notes

Reaction equation

HRID 539944 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.O.[Fe]>[NH2:1][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 5414-Nitrobenzaldehyde

Product 1

HCID 111584-AminobenzaldehydeYield 75%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 4-nitrobenzaldehyde (2.0 g, 0.133 mol) in acetic acid (150 mL) and water (15 mL) was added iron powder (1.48 g, 0.265 mol). The reaction was stirred overnight at room temperature. The mixture was filtered and extracted with dichloromethane (50 mL×3). Then the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 10% ethyl acetate in petroleum ether) to afford 1.2 g of the pure product (yield was 75%).

Workup

  1. filtrationThe mixture was filtered
  2. extractionextracted with dichloromethane (50 mL×3)
  3. dry with materialThen the organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (eluting with 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-46b72dd22fe0478a8777cb40ecc19dcd
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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