Hydrogen Peroxide → 2-Amino-6-fluoro-3-methylbenzoic acid

HRID 61273Notes

Reaction equation

HRID 61273 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4](=[O:13])C(=O)[NH:6]2.[OH:14]O>[OH-].[Na+]>[NH2:6][C:7]1[C:8]([CH3:11])=[CH:9][CH:10]=[C:2]([F:1])[C:3]=1[C:4]([OH:13])=[O:14]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 167912144-Fluoro-7-methyl-1H-indole-2,3-dione

Product 1

HCID 288812752-Amino-6-fluoro-3-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

4-Fluoro-7-methylindoline-2,3-dione (6.20 g, 34.6 mmol) in 1M NaOH (114 mL) was treated dropwise with 30% aq. H2O2 (20 mL), heated to 50° C. for 30 min, cooled to rt and filtered. The filtrate was adjusted to pH 4 with conc. HCl, cooled to 4° C. and filtered. The filter cake was dried under vacuum to provide the desired product. 1H NMR (CDCl3, 400 MHz) δ 7.15 (m, 1H), 6.40 (m, 1H), 2.15 (s, 3H).

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered
  3. temperaturecooled to 4° C.
  4. filtrationfiltered
  5. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-f38bea948b214af3bb5ee97c6feff430
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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