2-Amino-5-fluorobenzoic acid → Methyl 2-amino-5-fluorobenzoate

HRID 42035

Reaction equation

HRID 42035 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:13]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

3

Reactant 2

HCID 1014122-Amino-5-fluorobenzoic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 2783401Methyl 2-amino-5-fluorobenzoateYield 42%

Conditions

Temperature
100 °C

Procedure

A solution of 2-amino-5-fluorobenzoic acid (9.29 mmol, 1.440 g) in a mixture of HCl/MeOH (3N, 30 ml) was heated at 100° C. overnight. The solvent was evaporated and the crude mixture was extracted between DCM and K2CO3 saturated aqueous solution. The organic phase was evaporated and the crude mixture was purified by chromatography over SiO2 with hexane/ethyl acetate mixtures affording 0.650 g (yield 42%) of the expected product.

Workup

  1. customThe solvent was evaporated
  2. extractionthe crude mixture was extracted between DCM and K2CO3 saturated aqueous solution
  3. customThe organic phase was evaporated
  4. customthe crude mixture was purified by chromatography over SiO2 with hexane/ethyl acetate

Sources & evidence

ORD record
ord-40ac5aa251c046e8afc1ac46c6d942ed
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Linked notes

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