m-Chloroperbenzoic acid → HCID 54117372, compound

HRID 980834Notes

Reaction equation

HRID 980834 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH:7]=[CH:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11](=[O:12])[C:2]=12.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)(Cl)Cl>[N+:1]1([O-:25])[CH:6]=[CH:5][CH:4]=[C:3]2[CH:7]=[CH:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11](=[O:12])[C:2]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid3×HCID 13005083HCID 13005083, compound

Product 1

HCID 54117372HCID 54117372, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.04 grams (0.005 mole) of benzo[5,6]cyclohepta[1,2-b]pyridin-11-one in 20 milliliters of chloroform was added 1.19 grams (0.0055 mole) of m-chloroperbenzoic acid and the resulting solution stirred at room temperature for 24 hours. At this time an additional 0.6 gram of m-chloroperbenzoic acid was added and the mixture stirred for 5 hours; thereafter, another 0.3 gram of m-chloroperbenzoic acid was added and the mixture stirred overnight. The resulting reaction mixture was then washed twice with 10 percent aqueous sodium hydroxide, twice with water and the washed solution dried over magnesium sulfate. The mixture was filtered to remove drying agent and the solvent removed under reduced pressure to obtain 0.75 gram of benzo[5,6]cyclohepta[1,2-b]pyridin-11-one N-oxide intermediate as residue.

Workup

  1. stirringthe mixture stirred for 5 hours
  2. stirringthe mixture stirred overnight
  3. customThe resulting reaction mixture
  4. washwas then washed twice with 10 percent aqueous sodium hydroxide, twice with water
  5. dry with materialthe washed solution dried over magnesium sulfate
  6. filtrationThe mixture was filtered
  7. customto remove
  8. customdrying agent
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-56a0b8beafa347f59e1c97697351900e
Source dataset
uspto-grants-1987_01
Patent number
US04639457

Reaction notes

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