2-Isopropylpyridine → 1-Oxo-2-(propan-2-yl)-1lambda~5~-pyridine

HRID 471193

Reaction equation

HRID 471193 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([CH3:14])[CH3:13]>C(Cl)Cl>[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=1[O-:9])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 695232-IsopropylpyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 131720791-Oxo-2-(propan-2-yl)-1lambda~5~-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MCPBA (22.0 g) was added to a solution of 2-isopropylpyridine (example 85, step a) (9.1 g) in DCM (250 mL) and the resulting mixture stirred for 3 h. The reaction mixture was washed with saturated sodium bicarbonate solution (4×100 mL) and brine (100 mL), then dried over sodium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with ethyl acetate to 10% methanol in ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 3.9 g.

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution (4×100 mL) and brine (100 mL)
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification
  6. washeluting with ethyl acetate to 10% methanol in ethyl acetate gradient
  7. additionThe fractions containing product
  8. customevaporated

Sources & evidence

ORD record
ord-e39c48304864493484370eb858b53aa8
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Linked notes

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