Water → 2-Amino-6-fluorobenzoic acid

HRID 2198691Notes

Reaction equation

HRID 2198691 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#N.[OH-:11].[Na+].[OH2:13].S(=O)(=O)(O)O>C(O)C>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([NH2:1])[C:3]=1[C:4]([OH:13])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 5226592-Amino-6-fluorobenzonitrile

Product 1

HCID 5211422-Amino-6-fluorobenzoic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

56 parts of 2-amino-6-fluoro-benzonitrile, 33 parts of sodium hydroxide, 250 parts of water and 20 parts by volume of ethanol are refluxed for 8 hours. The pH is then brought to 3-4 with 20 percent strength by weight aqueous sulfuric acid and the precipitate formed is filtered off, washed with water and dried. The aqueous phase is extracted with methylene chloride, the solvent is stripped off under reduced pressure and the residue is dried, also under reduced pressure. In this way, a total of 58 parts of 6-fluoroanthranilic acid (90.9% of theory), of solidification point 165°-167° C., is obtained.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. washwashed with water
  4. customdried
  5. extractionThe aqueous phase is extracted with methylene chloride
  6. customthe residue is dried, also under reduced pressure

Sources & evidence

ORD record
ord-1690ac938c3b4693b766ab7d595132d6
Source dataset
uspto-grants-1982_11
Patent number
US04359428

Reaction notes

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