Pyridine → HCID 22563201, compound

HRID 982689Notes

Reaction equation

HRID 982689 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8][Br:9])=[CH:5][CH:4]=1)#[N:2].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[Br-:9].[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8][N+:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 1049PyridineHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 22563201HCID 22563201, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-cyanophenacyl bromide (10) (5.02 g, 22.2 mmol) in anhydrous acetonitrile (300 mL) was added pyridine (3.6 mL, 45.3 mmol) at room temperature. The mixture was stirred for 30 minutes. The precipitate was filtrated, washed with acetonitrile (20 mL) and dried under vacuum to give 1-(2-(4-cyano-phenyl)-2-oxo-ethyl)-pyridinium bromide (11) as a white powder (100%). 1H NMR (DMSO-d6) δ 6.56 (s, 2H), 8.21 (m, 6H), 8.76 (t, J=7.8, 1H), 9.03 (d, J=6.6, 2H).

Workup

  1. filtrationThe precipitate was filtrated
  2. washwashed with acetonitrile (20 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-64abd064b57b4fa28fc1d90b5510fb45
Source dataset
uspto-grants-2005_03
Patent number
US06861436B2

Reaction notes

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