Sodium Hydroxide → 4-bromo-N,2-dihydroxybenzamide

HRID 1988883Notes

Reaction equation

HRID 1988883 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([OH:12])[CH:3]=1.Cl.[NH2:14][OH:15].[OH-].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:14][OH:15])=[O:7])=[C:4]([OH:12])[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 13983552Methyl 4-bromo-2-hydroxybenzoate2×

Product 1

HCID 123854704-bromo-N,2-dihydroxybenzamideYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-bromo-2-hydroxybenzoate (Intermediate 22) (0.7 g) in dioxan (5 ml) was added dropwise to a solution of hydroxylamine hydrochloride (0.32 g) and sodium hydroxide (0.42 g) in water (10 ml) then stirred at room temp. for 18 h. The dioxan was removed under vacuum and the residue was stirred with 2N hydrochloric acid to give a precipitate which was collected by filtration, washed with water and dried to give the title compound as an off-white solid (0.63 g).

Workup

  1. customThe dioxan was removed under vacuum
  2. stirringthe residue was stirred with 2N hydrochloric acid
  3. customto give a precipitate which
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-22ce6c43493141e8a20e5823e7d9011a
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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