Pyridinium hydrochloride → HCID 68153395, compound

HRID 1946920Notes

Reaction equation

HRID 1946920 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16]C)=[N:14][CH:15]=2)=[CH2:9])[CH:5]=[CH:6][CH:7]=1.Cl.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)=[CH2:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 68153413HCID 68153413, compound

Product 1

HCID 68153395HCID 68153395, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
125 °C

Procedure

A sealed tube was charged with 5-[1-(3-bromo-phenyl)-vinyl]-2-methoxy-pyridine (600 mg) and pyridinium hydrochloride (3 g) freshly prepared. The tube was heated at 125° C. for 10 minutes, then the mixture was allowed to cool to room temperature. The crude was dissolved in dichloromethane (15 ml), the solution washed with hydrochloric acid (1N) (2×15 ml), dried over sodium sulphate and evaporated. The crude product was purified by flash chromatography eluting with cyclohexane/ethyl acetate. The 5-[1-(3-bromo-phenyl)-vinyl]-1H-pyridin-2-one was obtained as a colorless oil (366 mg, 64% of theory). MS (ISP): m/z=278 [M+H]+.

Workup

  1. customfreshly prepared
  2. temperatureto cool to room temperature
  3. washthe solution washed with hydrochloric acid (1N) (2×15 ml)
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe crude product was purified by flash chromatography
  7. washeluting with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-8ad99adcaaa24d2e8fbc41f1abf1a958
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

Loading…