Hydrochloric Acid → 2-Amino-4,5-difluorobenzoic acid

HRID 1031770Notes

Reaction equation

HRID 1031770 reaction equation
[OH-].[Na+].Cl.[NH2:4]O.[F:6][C:7]1[CH:8]=[C:9]2C(=O)[O:13][C:11](=[O:12])[C:10]2=[CH:16][C:17]=1[F:18].Cl>O>[F:6][C:7]1[CH:8]=[C:9]([NH2:4])[C:10](=[CH:16][C:17]=1[F:18])[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 6397454,5-Difluorophthalic Anhydride

Product 1

HCID 7359652-Amino-4,5-difluorobenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (7.5 g, 0.19 mol) and hydroxylamine hydrochloride (5.4 g, 0.0781 mol) were combined in 100 mL of water. 4,5-difluorophthalic anhydride (11.5 g, 0.062 mol) was added, and the reaction was heated to 90°-100° C. for 0.5 hour. The reaction was cooled, and acidified with HCl to a pH between 4 and 5. The precipitate was collected and dried to yield 10.2 g (91%) of 4,5-difluoroanthranilic acid.

Workup

  1. temperaturethe reaction was heated to 90°-100° C. for 0.5 hour
  2. temperatureThe reaction was cooled
  3. customThe precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-4472d2ebcd544da2bc807902528782da
Source dataset
uspto-grants-1990_09
Patent number
US04954639

Reaction notes

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