Water → 4-Amino-2-fluorobenzoic acid

HRID 1808180Notes

Reaction equation

HRID 1808180 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[C:4]([F:10])[CH:3]=1.[OH-:11].[K+].[OH2:13]>>[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([OH:13])=[O:11])=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 27834134-Amino-2-fluorobenzonitrile

Product 1

HCID 3026804-Amino-2-fluorobenzoic acidYield 84%

Procedure

A mixture of 4-amino-2-fluorobenzonitrile (25 g, 0.183 mmol) and potassium hydroxide (125 g, 2.23 mol) in water (350 ml) and industrial methylated spirit (50 ml) was heated at reflux for 48 hours. The solvent was evaporated in vacuo and the residue diluted with water and washed with DCM. The aqueous phase was acidified to pH 5.5 with concentrated HCl and the resultant precipitate collected by filtration to yield the title compound as a beige solid (23.94 g, 0.154 mol 84%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. customThe solvent was evaporated in vacuo
  4. additionthe residue diluted with water
  5. washwashed with DCM
  6. filtrationthe resultant precipitate collected by filtration

Sources & evidence

ORD record
ord-3b372f2a97e34f29bc5a8df70211488b
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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