Hydroxylamine → 5-Bromosalicylhydroxamic acid

HRID 1482862Notes

Reaction equation

HRID 1482862 reaction equation
[Br:1][C:2]1[CH:11]=[C:6]([C:7](OC)=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[NH2:13][OH:14]>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([NH:13][OH:14])=[O:8]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 77683Methyl 5-bromosalicylate

Product 1

HCID 220465-Bromosalicylhydroxamic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-bromosalicylate (5 g, 21.6 mmol) was dissolved in 90 mL 1,4-dioxane and 10 mL water. 10 mL 50% aqueous hydroxylamine solution was added and the mixture was stirred at ambient temperature for 24 hours. After concentrating the mixture under vacuum, water was added. The formed precipitate was filtered, washed with water and dried yielding 5-bromo-N,2-dihydroxybenzamide (4.12 g, 17.76 mmol) as off-white solid.

Workup

  1. concentrationAfter concentrating the mixture under vacuum, water
  2. additionwas added
  3. filtrationThe formed precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b8376e5484c44bdcb4cda9ecc9ea4db0
Source dataset
uspto-grants-2016_08
Patent number
US09416115B2

Reaction notes

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