m-Chloroperbenzoic acid → HCID 54574301, compound

HRID 980836Notes

Reaction equation

HRID 980836 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6]=[CH:7][C:8]3[C:9]([C:14](=[O:15])[C:4]=2[CH:3]=1)=[N:10][CH:11]=[CH:12][CH:13]=3.ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6]=[CH:7][C:8]3[C:9]([C:14](=[O:15])[C:4]=2[CH:3]=1)=[N+:10]([O-:26])[CH:11]=[CH:12][CH:13]=3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 21792630HCID 21792630, compound

Product 1

HCID 54574301HCID 54574301, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.15 grams (0.0075 mole) of 9-bromo-11-oxo-benzo[5,6]cyclohepta-[1,2-b]pyridine in 40 milliliters of chloroform was added 1.78 grams (0.0082 mole) of m-chloroperbenzoic acid and the resulting solution was stirred at room temperature for about 24 hours. At this time, an additional 0.9 gram of m-chloroperbenzoic acid oxidant was added and the stirring continued for 5 hours, after which time, yet another 0.45 gram of the oxidant was added and the stirring continued overnight at room temperature. The resulting mixture was washed twice with 10 percent aqueous sodium hydroxide and twice with water and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate concentrated at reduced pressure to obtain a residue. The latter was triturated with acetonitrile to obtain 1.37 grams of 9-bromo-11-oxo-benzo[5,6]cyclohepta[1,2-b]pyridine N-oxide intermediate.

Workup

  1. waitthe stirring continued for 5 hours
  2. additionafter which time, yet another 0.45 gram of the oxidant was added
  3. customthe stirring continued overnight
  4. customat room temperature
  5. washThe resulting mixture was washed twice with 10 percent aqueous sodium hydroxide and twice with water
  6. dry with materialdried over magnesium sulfate
  7. customThe drying agent was removed by filtration
  8. concentrationthe filtrate concentrated at reduced pressure
  9. customto obtain a residue
  10. customThe latter was triturated with acetonitrile

Sources & evidence

ORD record
ord-f55bbd43a5fa4110a79f1da4b9811beb
Source dataset
uspto-grants-1987_01
Patent number
US04639457

Reaction notes

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