5-Bromosalicylhydroxamic acid → HCID 178518981, compound

HRID 1482863Notes

Reaction equation

HRID 1482863 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([NH:9]O)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:12][N:9]=[C:7]([OH:8])[C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 220465-Bromosalicylhydroxamic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 178518981HCID 178518981, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-bromo-N,2-dihydroxybenzamide (4.12 g, 17.76 mmol) was suspended in 100 mL THF. Carbonyldiimidazole (5.76 g, 35.5 mmol) was added and the mixture was heated under reflux for three hours. The solvent was evaporated under vacuum, 100 mL water was added and the solution was acidified to pH 1 with 1N HCl under rapid stirring. The formed precipitate was filtered, washed with water and dried, giving 5-bromobenzo[d]isoxazol-3-ol (3.71 g, 17.3 mmol) as off-white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for three hours
  3. customThe solvent was evaporated under vacuum, 100 mL water
  4. additionwas added
  5. filtrationThe formed precipitate was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-81ebe21a11a443078bdedfaad161087c
Source dataset
uspto-grants-2016_08
Patent number
US09416115B2

Reaction notes

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