m-Chloroperbenzoic acid → HCID 13688051, compound

HRID 1722997Notes

Reaction equation

HRID 1722997 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[C:3]=1[C:10]#[N:11].ClC1C=C(C=CC=1)C(OO)=[O:17]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N+:5]([O-:17])=[C:4]([CH3:9])[C:3]=1[C:10]#[N:11]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13688050HCID 13688050, compound

Product 1

HCID 13688051HCID 13688051, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 g (0.3 mol) of 4-chloro-3-cyano-2,6-dimethylpyridine were dissolved in 1 L of dichloromethane and, at room temperature, 130 g (0.6 mol) of 80% pure m-chloroperoxybenzoic acid were added in portions, and the mixture was stirred overnight and the precipitated m-chlorobenzoic acid was filtered off. Water was added to the filtrate, the pH was adjusted to 12 with solid potassium hydroxide, and the two phases were shaken together to extract. The dichloromethane phase was separated off, dried over sodium sulfate, filtered and evaporated. 4-Chloro-3-cyano-2,6dimethylpyridine 1-oxide was obtained as a solid compound which sintered at 140° C. Yield: 49.3 g (90% of theory).

Workup

  1. filtrationthe precipitated m-chlorobenzoic acid was filtered off
  2. additionWater was added to the filtrate
  3. stirringthe two phases were shaken together
  4. extractionto extract
  5. customThe dichloromethane phase was separated off
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-27fb685bc20d4e4c83a1e0cb00ad6697
Source dataset
uspto-grants-1989_08
Patent number
US04859663

Reaction notes

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