2-Fluoro-6-nitrophenol → 2-Amino-6-fluorophenol

HRID 2067088Notes

Reaction equation

HRID 2067088 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[OH:11].C([O-])=O.[NH4+]>CO.[Pd]>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[OH:11]

Participants

5

Reactant 2

HCID 737102-Fluoro-6-nitrophenolHCID 2723923Ammonium formate

Product 1

HCID 6435622-Amino-6-fluorophenolYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a three neck flask, fitted with a magnetic stirrer, under inert atmosphere, a suspension of 2-fluoro-6-nitrophenol (5 g, 31.83 mmol), ammonium formate (6 g, 95.50 mmol) and Pd—C (10% w/w, 0.34 g, 3.2 mmol) in MeOH (100 ml) is stirred 0.5 h at room temperature. The reaction mixture is filtered through celite and concentrated in vacuo to give 2-amino-6-fluorophenol 1 (4 g) which is used in the next step without any further purification.

Workup

  1. customIn a three neck flask, fitted with a magnetic stirrer, under inert atmosphere
  2. filtrationThe reaction mixture is filtered through celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03e8806e960947f4af63cd2eadbf813c
Source dataset
uspto-grants-2012_10
Patent number
US08293775B2

Reaction notes

Loading…