Potassium Hydroxide → HCID 22176444, compound

HRID 965875Notes

Reaction equation

HRID 965875 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[N:3]=1.[OH-:10].[K+]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[N+:3]=1[O-:10]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 129548002-Bromo-6-ethylpyridine

Product 1

HCID 22176444HCID 22176444, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-bromo-6-ethyl-pyridine (15.4 g, 82.8 mmol) (S. G. Davies and M. R. Shipton, J. Chem. Soc., Perkin Trans. 1, 1991, 3, 501) in acetic acid (15 ml) peracetic acid (26 ml of a 39%) solution) was added maintaining T<50° C. After completed addition the mixture was stirred at 50° C. for 5 hr and then cooled to rt. Crushed ice (40 g) was added and the mixture was made basic (pH 12) using 40% KOH solution. After extraction with CHCl3 (6×60 ml) the combined organic phases were dried (Na2CO3) and evaporated to give 20.0 g (>100%) of the title compound, MS: m/e=201 (M+) as a yellow oil.

Workup

  1. additionaddition the mixture
  2. temperaturecooled to rt
  3. extractionAfter extraction with CHCl3 (6×60 ml) the combined organic phases
  4. dry with materialwere dried (Na2CO3)
  5. customevaporated

Sources & evidence

ORD record
ord-e533fd8a7f244e98a28135262bce7c85
Source dataset
uspto-grants-2005_10
Patent number
US06951875B2

Reaction notes

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