Hydrochloric Acid → 2-Amino-3-chloro-5-fluorobenzoic acid

HRID 1041729Notes

Reaction equation

HRID 1041729 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:13])[CH:5]=[C:6]2[C:10]=1[NH:9]C(=O)[C:7]2=[O:12].[OH:14]O.Cl>[OH-].[Na+]>[NH2:9][C:10]1[C:2]([Cl:1])=[CH:3][C:4]([F:13])=[CH:5][C:6]=1[C:7]([OH:12])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 16793679HCID 16793679, compound

Product 1

HCID 289741482-Amino-3-chloro-5-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 7-chloro-5-fluoro-1H-indole-2,3-dione (270 mg) in 1 M sodium hydroxide solution (5 mL) was treated with 30% hydrogen peroxide (5 mL) via dropwise addition. After one hour of stirring, the reaction was acidified with HCl to pH 1, and extracted three times with ethyl acetate. The combined organic layers were dried with sodium sulfate, and concentrated in vacuo to provide 200 mg of 2-amino-3-chloro-5-fluoro-benzoic acid.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c31c0868b74449e943750cf469db363
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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