Ammonia → 2-Amino-5-fluorobenzoic acid

HRID 259921Notes

Reaction equation

HRID 259921 reaction equation
[NH3:1].[F:2][C:3]1[CH:4]=[CH:5][C:6](Br)=[C:7]([CH:11]=1)[C:8]([O-:10])=[O:9]>Cl[Cu]>[F:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([NH2:1])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 70155575-Fluoro-2-bromobenzoate

Product 1

HCID 1014122-Amino-5-fluorobenzoic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

Example 9 is repeated precisely, the only difference being that one part of CuCl is added to the initial ammonia solution charge. After the 5-fluoro-2-bromobenzoate solution has been metered in and the batch worked up, 144 parts of 5-fluoroanthranilic acid of m.p. 176.5°-177.5° C. are obtained with a purity of 91.9% (HPLC), corresponding to a yield of 85.4% of theory, based on the 5-fluoro-2-bromobenzoic acid employed.

Workup

  1. additioncharge

Sources & evidence

ORD record
ord-0d5c3bb66e8b4bc8b7db9d2987871fc0
Source dataset
uspto-grants-1996_06
Patent number
US05523472

Reaction notes

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