m-Chloroperbenzoic acid → 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one 1-Oxide

HRID 840250Notes

Reaction equation

HRID 840250 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[O:16])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1.ClC1C=C(C=CC=1)C(OO)=[O:23]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[O:16])[C:10]3=[N+:11]([O-:23])[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 98162608-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one

Product 1

HCID 107537998-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one 1-Oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 25.1 grams (0.103 mole) of 8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one in 175 ml of dry CH2Cl2 at 0° C. under an argon atmosphere was added dropwise over 70 minutes a solution of 24.12 grams of 3-chloroperoxy-benzoic acid in 150 ml of CH2Cl2. After the addition the solution was stirred for ½ hour after which the ice bath was removed. After two days the reaction was poured into 1.0 N aqueous NaOH and extracted with CH2Cl2. The organic portions were combined, washed once with water, dried over MgSO4, filtered and concentrated in vacuo. The resultant product was triturated with isopropyl ether and filtered to provide 25.8 grams (96%) yield of the title compound.

Workup

  1. additionAfter the addition the solution
  2. customwas removed
  3. additionAfter two days the reaction was poured into 1.0 N aqueous NaOH
  4. extractionextracted with CH2Cl2
  5. washwashed once with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resultant product was triturated with isopropyl ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-94e1a4c43fe542caa0c1ddc8f8b318fc
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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