m-Chloroperbenzoic acid → 2,6-Dimethyl-4-(2-(4 nitrophenyl)ethyl) pyridine N-oxide

HRID 365697Notes

Reaction equation

HRID 365697 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH3:19])[N:3]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)(Cl)Cl>[CH3:19][C:4]1[CH:5]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH:7]=[C:2]([CH3:1])[N+:3]=1[O-:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178058592,6-Dimethyl-4-(2-(4-nitrophenyl)ethyl) pyridine

Product 1

HCID 536611612,6-Dimethyl-4-(2-(4 nitrophenyl)ethyl) pyridine N-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound (3) (22.82 g, 84.5 mmol) was dissolved in chloroform (100 ml), and 16 g (94 mmol) of m-chloroperbenzoic acid (mCPBA) was addedin small portions at RT over a period of 30 min. The mixture was stirred for an additional 2 h and after a negative TLC test for the starting material it was worked up by partitioning between sat. sodium hydrogen carbonate and chloroform. The combined chloroform extracts (3×200 ml) were evaporated yielding a light yellow solid material that was TLC pure.

Workup

  1. customat RT
  2. customof 30 min
  3. customby partitioning between sat. sodium hydrogen carbonate and chloroform
  4. customwere evaporated
  5. customyielding a light yellow solid material that

Sources & evidence

ORD record
ord-1e61acbc014c443d96c9d94f0d42cda3
Source dataset
uspto-grants-2000_10
Patent number
US06127529

Reaction notes

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