m-Chloroperbenzoic acid → 2-Pyridinecarboxylic acid, 5-methyl-, 1-oxide

HRID 631996

Reaction equation

HRID 631996 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[N:17][CH:18]=1>C(Cl)Cl>[CH3:12][C:13]1[CH:18]=[N+:17]([O-:9])[C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1995755-Methylpicolinic acid

Product 1

HCID 866747432-Pyridinecarboxylic acid, 5-methyl-, 1-oxideYield 40.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-CPBA (CAN 937-14-4, 5.0 g, 29.2 mmol) was added to a solution of 5-methyl-pyridine-2-carboxylic acid (CAN 4434-13-3, 2.0 g, 14.6 mmol) in methylene chloride (50 mL) and the mixture was stirred overnight at room temperature. The solid was filtered off, quenched with a saturated solution of sodium thiosulfate (50 mL), and the mixture was extracted with methylene chloride (3×60 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated in vacuo to give yellow solid which was washed with ether (5×20 mL) to give the product (0.9 g, 40.3%); MS (EI): m/e=154.1 [M+H]+.

Workup

  1. filtrationThe solid was filtered off
  2. customquenched with a saturated solution of sodium thiosulfate (50 mL)
  3. extractionthe mixture was extracted with methylene chloride (3×60 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give yellow solid which
  7. washwas washed with ether (5×20 mL)

Sources & evidence

ORD record
ord-9991ac013f574c5d83b5ab1d382a0495
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Linked notes

Loading…