Ammonia → 3-Amino-4-fluorophenol

HRID 1596243Notes

Reaction equation

HRID 1596243 reaction equation
N.[F:2][C:3]1[CH:9]=[CH:8][C:7]([O:10]C(OC)=O)=[CH:6][C:4]=1[NH2:5]>CO>[F:2][C:3]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:4]=1[NH2:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 217015692-Fluoro-5-methoxycarbonyloxyaniline

Product 1

HCID 135191803-Amino-4-fluorophenolYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated aqueous ammonia (15 ml) was added to a solution of 2-fluoro-5-methoxycarbonyloxyaniline (400 mg, 2.16 mmol) in methanol (10 ml). The mixture was stirred for 2 hours and most of the solvent was removed by evaporation. The resulting suspension was diluted with water, acidified to pH7 and extracted with ethyl acetate. The organic extracts were washed with water, dried (MgSO4) and solvent removed by evaporation to give 2-fluoro-5-hydroxyaniline (200 mg, 73%).

Workup

  1. customwas removed by evaporation
  2. additionThe resulting suspension was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with water
  5. dry with materialdried (MgSO4) and solvent
  6. customremoved by evaporation

Sources & evidence

ORD record
ord-ca1253032bf3453b8fcabf92739bff90
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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