Acetic Acid → HCID 178474109, compound

HRID 2071633Notes

Reaction equation

HRID 2071633 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N:6]=1)(=[O:3])[CH3:2].C(O)(=[O:14])C.C(OO)(=O)C>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N+:6]=1[O-:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6585Peracetic AcidHCID 10353221N-(6-bromopyridin-2-yl)acetamide

Product 1

HCID 178474109HCID 178474109, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

23.4 gms (0.109 mole) of 2-acetamido-6-bromopyridine was dissolved in 200 ml. of glacial acetic acid containing 27.6 ml (0.218 mole) of 7.9M peracetic acid and the solution was heated at 70° C for 2 hours and at 55° C for 19 hours. The reaction mixture was diluted with 1600 ml water and the solution was then concentrated in vacuo to 550 ml. 8.6% of unreacted-2-acetamido-6-bromopyridine was removed by filtration. The solvent was evaporated from the filtrate giving an 83% yield of impure 2-acetamido-6-bromopyridine-1-oxide which was purified by treatment with activated charcoal to remove the yellow impurity and subsequently recrystallized from 2-propanol. A second recrystallization from 2-propanol gave fine white needles, m.p.=180.0°-180.5° C.

Workup

  1. concentrationthe solution was then concentrated in vacuo to 550 ml
  2. custom8.6% of unreacted-2-acetamido-6-bromopyridine was removed by filtration
  3. customThe solvent was evaporated from the filtrate

Sources & evidence

ORD record
ord-e6585a5b41174eb9a56ea81f9ecc4de0
Source dataset
uspto-grants-1977_09
Patent number
US04048181

Reaction notes

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