Hydroxylamine → 3,4-difluoro-N,2-dihydroxybenzamide

HRID 245526Notes

Reaction equation

HRID 245526 reaction equation
[NH2:1][OH:2].[F:3][C:4]1[C:5]([OH:15])=[C:6]([CH:11]=[CH:12][C:13]=1[F:14])[C:7](OC)=[O:8]>O1CCOCC1>[F:3][C:4]1[C:5]([OH:15])=[C:6]([CH:11]=[CH:12][C:13]=1[F:14])[C:7]([NH:1][OH:2])=[O:8]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 46311128Methyl 3,4-difluoro-2-hydroxybenzoate2×

Product 1

HCID 866581193,4-difluoro-N,2-dihydroxybenzamideYield 101.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of hydroxylamine (50% in water) (50 ml, 816 mmol) was added to a solution of methyl 3,4-difluoro-2-hydroxybenzoate (7.75 g, 41.2 mmol) (Intermediate 526) in dioxane (200 ml) and the mixture was stirred at room temperature for 3 days. The mixture was partitioned between water and EtOAc. The aqueous layer was acidified with concentrated HCl and extracted with EtOAc twice more. The EtOAc layers were washed with brine, combined and concentrated to give 7.9 g of a solid.

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. extractionextracted with EtOAc twice more
  3. washThe EtOAc layers were washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2613f28fac264875a25302a439afe995
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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