m-Chloroperbenzoic acid → 4-Cyclopropyl-3-iodopyridine 1-oxide

HRID 523613Notes

Reaction equation

HRID 523613 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]1([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[I:21])[CH2:14][CH2:13]1>C(Cl)Cl>[CH:12]1([C:15]2[CH:20]=[CH:19][N+:18]([O-:9])=[CH:17][C:16]=2[I:21])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 668018874-Cyclopropyl-3-iodopyridine

Product 1

HCID 709832464-Cyclopropyl-3-iodopyridine 1-oxideYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (408 mg, 2.36 mmol) was added to the solution of 4-cyclopropyl-3-iodopyridine (I-30a: 200 mg. 0.816 mmol) in DCM (10 mL) and the resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC. The reaction mixture was quenched with ice and diluted with DCM. The organic layer was washed with dilute NaOH solution, water and brine solution, dried over sodium sulphate and concentrated to afford 200 mg of the product (94.7% yield).

Workup

  1. customThe reaction mixture was quenched with ice
  2. additiondiluted with DCM
  3. washThe organic layer was washed with dilute NaOH solution, water and brine solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-95ae64408357478ab735cab158160275
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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