m-Chloroperbenzoic acid → 3-Ethynyl-pyridine 1-oxide

HRID 351736Notes

Reaction equation

HRID 351736 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].ClC1C=C(C=CC=1)C(OO)=[O:14].[OH-].[Ca+2].[OH-]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[N+:5]([O-:14])[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 1860033-EthynylpyridineHCID 6093208Calcium Hydroxide

Product 1

HCID 569723343-Ethynyl-pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-ethynylpyridine in methylene chloride (5 mL/mmol) at room temperature was added m-chloroperoxybenzoic acid (m-CPBA, 70% purity, 1.2 eq) and the resulting mixture was stirred for 2 hours. A further amount of m-CPBA was added (0.25 eq) and stirring was continued for 1 hour. Calcium hydroxide was added (2 eq) and after 15 minutes the mixture was filtered through celite and the filtrate was evaporated. The solid residue was stirred in ether for 3 hours and filtered to afford the 3-ethynylpyridine N-oxide compound as a white solid.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. filtrationafter 15 minutes the mixture was filtered through celite
  4. customthe filtrate was evaporated
  5. stirringThe solid residue was stirred in ether for 3 hours
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5042c575a2b54e77a4e7e5fb3921d199
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

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