Pyridine → HCID 12266212, compound

HRID 1160092Notes

Reaction equation

HRID 1160092 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:4].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[Br-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)[CH2:2][N+:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 692722-Bromo-4'-methylacetophenone

Product 1

HCID 12266212HCID 12266212, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-bromo-4′-methyl-acetophenone (784 mg, 3.31 mmol) in acetone (7 mL) was added pyridine (243 μl, 3.02 mmol). The mixture was refluxed for 2 hours and the white solid formed was isolated by filtration and rinsed with Et2O in 100% yield: mp 213-214° C.; 1H NMR 400 MHz (DMSO-d6) δ 2.45 (s, 3H), 6.50 (s, 2H), 7.48 (d, 2H, J=7.3 Hz), 7.97 (d, 2H, J=7.8 Hz), 8.28 (m, 2H), 8.74 (t, 1H, J=7.3 Hz), 9.03 (d, 2H, J=5.9 Hz); Elem. anal. found: C, 55.46; H, 5.40; N, 4.85% (calcd for C14H14BrNO ½H2O: C, 55.83; H, 5.02; N, 4.65%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customthe white solid formed
  3. customwas isolated by filtration
  4. washrinsed with Et2O in 100% yield

Sources & evidence

ORD record
ord-6abb32719af54bb89c554469e14c9a81
Source dataset
uspto-grants-2010_10
Patent number
US07816352B2

Reaction notes

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