m-Chloroperbenzoic acid → HCID 18722386, compound

HRID 1368866Notes

Reaction equation

HRID 1368866 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[C:8](=[O:18])[C:5]2=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[C:8](=[O:18])[C:5]2=[N+:6]([O-:27])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 9818617HCID 9818617, compound

Product 1

HCID 18722386HCID 18722386, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a solution of 3-bromo-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (2 g) (6.2 mmoles) in anhydrous dichloromethane (14 ml) at 0° C. and under an argon atmosphere, was added a solution of 3-chloroperbenzoic acid (1.76 g) (10.4 mmoles) in anhydrous dichloromethane (35 ml) dropwise over a period of 30 minutes. The mixture was allowed to warm to room temperature and after 18 h additional 3-chloroperbenzoic acid (0.88 g) (5.2 mmoles) in anhydrous dichloromethane (25 ml) was added and the mixture was stirred for a total of 42 h. The mixture was diluted with dichloromethane and washed with 1N NaOH (200 ml). The aqueous layer was extracted with additional dichloromethane (2X200 ml) and the combined organic layers were dried over magnesium sulfate, filtered and evaporated to dryness. The product was chromatographed on silica gel using 0.25%-0.5%-1% (10% conc. NH4OH in methanol)dichloromethane as the eluant to give the title compound (Yield:1.386 g, 66%): ESIMS; m/z 338.1 (MH+); δc (CDCl3) CH2: 30.5, 34.0; CH: 126.9, 127.6, 130.3, 132.5, 140.4; C: 121.0, 135.1, 138.3, 139.7, 141.6, 145.3, 188.0 ppm.

Workup

  1. additionwas added
  2. washwashed with 1N NaOH (200 ml)
  3. extractionThe aqueous layer was extracted with additional dichloromethane (2X200 ml)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe product was chromatographed on silica gel using 0.25%-0.5%-1% (10% conc. NH4OH in methanol)dichloromethane as the eluant

Sources & evidence

ORD record
ord-13ae8314fbbb466fa79a7b511d1cdc9b
Source dataset
uspto-grants-2003_06
Patent number
US06576639B1

Reaction notes

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