Ammonia → 2-Aminobenzaldehyde

HRID 869721Notes

Reaction equation

HRID 869721 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O-])=O.N>C(O)C.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 111012-Nitrobenzaldehyde

Product 1

HCID 682552-Aminobenzaldehyde

Reagents, catalysts & solvents 3

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-nitrobenzaldehyde (10.0 g, 66.2 mmol) and iron(II) sulfate heptahydrate (129 g, 464 mmol) in ethanol (150 mL) and water (150 mL) was heated at 100° C. for 5 min, and then 28% aqueous ammonia (173 mL) was added dropwise carefully at same temperature. The reaction mixture was filtrated through Celite with diethyl ether. The organic layer was washed with water and saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo to give the crude 2-aminobenzaldehyde.

Workup

  1. filtrationThe reaction mixture was filtrated through Celite with diethyl ether
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0803cb2fcce340ef847ee7ba8f8b3e19
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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