Acetone → HCID 67316339, compound

HRID 1014179Notes

Reaction equation

HRID 1014179 reaction equation
C[C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:17]([Br:20])[CH:18]=[CH2:19].C[C:22](C)=[O:23]>>[Br-:20].[CH3:22][O:23][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[N+:13]([CH2:17][CH:18]=[CH2:19])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 180AcetoneHCID 7841Allyl bromideHCID 21071594HCID 21071594, compound2×

Product 1

HCID 67316339HCID 67316339, compoundYield 99%

Conditions

Temperature
60 °C

Procedure

To acetone (300 mL) was added 3-(3-methyl-4-nitrophenyl)pyridine (Intermediate B9, 20.25 g, 88.0 mmol)) and allyl bromide (42.6 g, 352.2 mmol, Aldrich), and the reaction was stirred at 60° C. for 12 h. Filtration removed the liquids and washing with MeOH (2×20 mL) afforded 3-[3-(methyloxy)-4-nitrophenyl]-1-(2-propen-1-yl)pyridinium bromide as a yellow solid (30.8 g, 99% yield).

Workup

  1. filtrationFiltration
  2. customremoved the liquids
  3. washwashing with MeOH (2×20 mL)

Sources & evidence

ORD record
ord-538c432c21694d398e92c90a7de8a549
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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