m-Chloroperbenzoic acid → HCID 67084377, compound

HRID 1438198Notes

Reaction equation

HRID 1438198 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, 3H), 2.89 (q, J=7.5 Hz, 2H), 3.82 (s, 3H), 6.86 (d, J=8.4 Hz, 1H), 7.11 (d, J=8.3 Hz, 1H), 8.04 (s, 1H).

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-1979383197c44bf2a8a6d937e8a8d97c
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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