Ammonia → 2-Amino-4-bromobenzaldehyde

HRID 1359417Notes

Reaction equation

HRID 1359417 reaction equation
N.[N+:2]([C:5]1[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])([O-])=O.CO.Cl>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].O>[NH2:2][C:5]1[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 887MethanolHCID 6080994-Bromo-2-nitrobenzaldehyde

Product 1

HCID 179145982-Amino-4-bromobenzaldehydeYield 89.7%

Reagents, catalysts & solvents 2

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 962WaterSolvent

Procedure

16.1 ml of an aqueous 29% ammonia solution was added to a mixture of 5.0 g of 2-nitro-4-bromobenzaldehyde, 60.4 g of iron (II) sulfate heptahydrate, 200 ml of methanol, 100 ml of water and 335 μl of concentrated hydrochloric acid in an oil bath kept at 90° C., followed by heating under stirring for 10 minutes. After cooling as it was, insoluble matters were filtered through Celite and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine and the solvent was removed, to give 3.9 g of the target compound.

Workup

  1. customkept at 90° C.
  2. temperatureby heating
  3. temperatureAfter cooling as it
  4. filtrationinsoluble matters were filtered through Celite
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe organic phase was washed with brine
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-551f79048f014245b49e52d82c0e8fd6
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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