m-Chloroperbenzoic acid → HCID 67084377, compound

HRID 2387009Notes

Reaction equation

HRID 2387009 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][N:15]=1)[CH3:13]>C(Cl)(Cl)Cl>[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][N+:15]=1[O-:6])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 450796842-Ethyl-5-methoxypyridine

Product 1

HCID 67084377HCID 67084377, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperoxybenzoic acid (5.66 g, 32.8 mmol) was added to a stirred solution of 2-ethyl-5-methoxy-pyridine (3 g, 22 mmol) dissolved in CHCl3 (100 mL). The reaction was stirred at room temperature for 3 hours and then quenched with satd Na2SO3. The reaction mixture was partitioned between H2O and CH2Cl2. The organic layer was washed with 1N NaOH, dried over Na2SO4 and concentrated to an oil (3.3 g, 99%). 1H NMR (400 MHz, CDCl3): δ 1.29 (t, J=7.5 Hz, 3 H), 2.89 (q, J=7.5 Hz, 2 H), 3.82 (s, 3 H), 6.86 (d, J=8.4 Hz, 1 H), 7.11 (d, J=8.3 Hz, 1 H), 8.04 (s, 1 H).

Workup

  1. customquenched with satd Na2SO3
  2. customThe reaction mixture was partitioned between H2O and CH2Cl2
  3. washThe organic layer was washed with 1N NaOH
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil (3.3 g, 99%)

Sources & evidence

ORD record
ord-8097c8bb88384cbda001991dd8366dd7
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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