Acetic Acid → Methyl 2-amino-5-fluoro-3-hydroxybenzoate

HRID 249906Notes

Reaction equation

HRID 249906 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:15])[C:5]([N+:12]([O-])=O)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(O)(=O)C>CO.[Pd]>[NH2:12][C:5]1[C:4]([OH:15])=[CH:3][C:2]([F:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66874176Methyl 5-fluoro-3-hydroxy-2-nitrobenzoate

Product 1

HCID 66873693Methyl 2-amino-5-fluoro-3-hydroxybenzoateYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 5-fluoro-3-hydroxy-2-nitrobenzoate (1.15 g, 5.34 mmol) in a mixture of CH3OH and glacial acetic acid (3:1, 40 mL) was added 10 wt % palladium on activated charcoal (0.20 g, 17 wt %). The suspension was placed in a Parr hydrogenation apparatus under a H2 atmosphere at 50 psi for 1.5 h. The suspension was filtered through diatomaceous earth eluting with CH2Cl2/CH3OH (9:1, 100 mL). Purification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes) afforded methyl 2-amino-5-fluoro-3-hydroxybenzoate (0.80 g, 83%) as a white solid. 1H NMR and MS consistent.

Workup

  1. filtrationThe suspension was filtered through diatomaceous earth
  2. washeluting with CH2Cl2/CH3OH (9:1, 100 mL)
  3. customPurification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-401a8fb146d24bffac2029edbf1767ac
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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