m-Chloroperbenzoic acid → HCID 13772001, compound

HRID 980832Notes

Reaction equation

HRID 980832 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7](=[O:16])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][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[C:7](=[O:16])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:2]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 1203582HCID 1203582, compound

Product 1

HCID 13772001HCID 13772001, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2.07 grams (0.01 mole) of benzo[4,5]cyclohepta[1,2-b]pyridin-5-one in 25 milliliters of chloroform was added dropwise, a solution of 2.0 grams (0.01 mole) of m-chloroperbenzoic acid in 30 milliliters of chloroform and the resulting solution stirred for 7 hours at room temperature. At this time an additional 0.5 gram of m-chloroperbenzoic acid was added and the mixture stirred overnight at room temperature. The resulting reaction mixture was washed successively with two 100 milliliter portions of 10 percent aqueous sodium hydroxide and two 100 milliliter portions of water and then dried over magnesium sulfate. The dried solution was filtered to remove the drying agent and the chloroform was vaporized to obtain 2.23 grams of a benzo[4,5]cyclohepta[1,2-b]pyridin-5-one N-oxide intermediate.

Workup

  1. customThe resulting reaction mixture
  2. washwas washed successively with two 100 milliliter portions of 10 percent aqueous sodium hydroxide and two 100 milliliter portions of water
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe dried solution was filtered
  5. customto remove the drying agent

Sources & evidence

ORD record
ord-82bb1f0868504213ad82ef97ce3a944d
Source dataset
uspto-grants-1987_01
Patent number
US04639457

Reaction notes

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