Ammonium Hydroxide → 2-Amino-6-bromo-4-nitrophenol

HRID 583188Notes

Reaction equation

HRID 583188 reaction equation
[NH4+].[Cl-].[NH4+].[OH-].[Br:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([N+:15]([O-])=O)[C:7]=1[OH:18]>O>[NH2:15][C:8]1[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:6]([Br:5])[C:7]=1[OH:18]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 2646412-Bromo-4,6-dinitrophenol

Product 1

HCID 152196842-Amino-6-bromo-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

10 g of NH4Cl and 2 mL of NH4OH were added to a solution of 4.7 g of 2-bromo-4,6-dinitro-phenol and 50 mL of water. The mixture was heated to 85° C., and then cooled to 70° C. At this point 5.2 g of Na2S-9H2O was added, keeping reaction between 80-85° C. After addition, reaction was heated for 2 h at 85° C. Solution was then cooled in ice bath, and resulting precipitate was collected via filtration. The solid was then placed in 30 mL of water, brought to a boil, acidified with AcOH, along with 170 mg of norit being added. The solution was filtered hot, then cooled with 1.97 g of title compound crystalizing out of solution. The compound was carried on without further purification.

Workup

  1. temperaturecooled to 70° C
  2. customreaction between 80-85° C
  3. additionAfter addition, reaction
  4. temperaturewas heated for 2 h at 85° C
  5. temperatureSolution was then cooled in ice bath
  6. customresulting precipitate
  7. filtrationwas collected via filtration
  8. additionadded
  9. filtrationThe solution was filtered hot
  10. temperaturecooled with 1.97 g of title compound
  11. customcrystalizing out of solution
  12. customThe compound was carried on without further purification

Sources & evidence

ORD record
ord-e577c60773614272b8ed6e35dc53d310
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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