Hydrochloric Acid → 2-Amino-5-fluorobenzoic acid

HRID 238226

Reaction equation

HRID 238226 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7]C(=O)[C:5]2=[O:12].[OH:13]O.Cl>[OH-].[Na+]>[NH2:7][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[C:5]([OH:12])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 2365665-Fluoroisatin

Product 1

HCID 1014122-Amino-5-fluorobenzoic acidYield 80.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A stirred solution of 5-fluoroisatin (39 g, 0.236 mol) in NaOH (5%, 500 mL) was treated dropwise over 10 min with 30% H2O2 (57 g, calculated to contain 17 g, 0.5 mol). After another 20 min of being stirred, during which became warm and effervesced, the solution was cooled in an ice-bath and acidified to pH=4 with 3 M HCl. The precipitated solid was collected and dried in air to obtain 2-amino-5-fluoro-benzoic acid 1 as a beige powder (29.6 g, 80%). 1H NMR (DMSO-d6) δ 7.3-8.2 (m, 2H), 7.08 (d, J=9 Hz, 1H), 6.63 (d, J=9 Hz, 2H), 2.13 (s, 3H).

Workup

  1. temperaturebecame warm
  2. temperatureeffervesced, the solution was cooled in an ice-bath
  3. customThe precipitated solid was collected
  4. customdried in air

Sources & evidence

ORD record
ord-f2002e4ddc1444d886a6b3f677148a94
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Linked notes

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