4,5-Dichloro-2-nitrobenzaldehyde → 2-Amino-4,5-dichlorobenzaldehyde

HRID 726642

Reaction equation

HRID 726642 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([N+:11]([O-])=O)=[CH:8][C:9]=1[Cl:10])[CH:5]=[O:6]>C(O)C.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([NH2:11])=[CH:8][C:9]=1[Cl:10])[CH:5]=[O:6]

Participants

5

Reactant 1

HCID 27492464,5-Dichloro-2-nitrobenzaldehyde

Product 1

HCID 8180132-Amino-4,5-dichlorobenzaldehydeYield 86.8%

Reagents, catalysts & solvents 3

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3,4-Dichloro-6-nitrobenzaldehyde (4.40 g, 20 mmol) was dissolved in 50% aqueous ethanol (200 ml) at 50°-60° C. and the solution was added to a solution of iron(II) sulfate heptahydrate (27.8 g, 100 mmol) in water (200 ml) at 90° C. Concentrated (25%) aqueous ammonia (50 ml) was added in several portions with intensive stirring while the temperature was kept close to the boiling point. The mixture was refluxed for 5-10 min. and cooled. The precipitate was filtered off and washed with ethanol. The filtrate was concentrated in vacuo until most of the ethanol was removed. The resulting precipitate was collected, washed with water and dried in vacuo at 40°-50° C. to give 3.3 g of 3,4-dichloro-6-aminobenzaldehyde.

Workup

  1. concentrationConcentrated (25%) aqueous ammonia (50 ml)
  2. additionwas added in several portions
  3. customwas kept close to the boiling point
  4. temperatureThe mixture was refluxed for 5-10 min.
  5. temperaturecooled
  6. filtrationThe precipitate was filtered off
  7. washwashed with ethanol
  8. concentrationThe filtrate was concentrated in vacuo until most of the ethanol
  9. customwas removed
  10. customThe resulting precipitate was collected
  11. washwashed with water
  12. customdried in vacuo at 40°-50° C.

Sources & evidence

ORD record
ord-2e39e3bdfd2e4393baa17f651f3c6417
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Linked notes

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