Potassium Carbonate → 5-Amino-2-chlorophenol

HRID 491606Notes

Reaction equation

HRID 491606 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[OH:11].Cl[Sn]Cl.C([O-])([O-])=O.[K+].[K+]>CCO>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([OH:11])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24479Stannous ChlorideHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 806765-Amino-2-chlorophenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-5-nitrophenol (3.06 g, 17.6 mmol) and SnCl2 (10.0 g, 52.8 mmol) in EtOH (120 mL) were heated for 10 h at 80° C. The reaction was treated with 1N K2CO3 (aq) and filtered through Celite. Most of the solvent was removed under vacuum. The crude was treated with saturated NaHCO3 and extracted with EtOAc twice. The organic layers were washed with water then brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield the title compound as a brown-green solid.

Workup

  1. filtrationfiltered through Celite
  2. customMost of the solvent was removed under vacuum
  3. additionThe crude was treated with saturated NaHCO3
  4. extractionextracted with EtOAc twice
  5. washThe organic layers were washed with water
  6. dry with materialbrine, dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40e2ede578984500a4e7dd5bceb82a94
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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