2-Methylpyridine → 1-Dodec-9-ynyl-2-methyl-pyridinium bromide

HRID 84326Notes

Reaction equation

HRID 84326 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[C:11][CH2:12][CH3:13].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]>C(#N)C>[Br-:1].[CH2:2]([N+:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[C:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 79752-MethylpyridineHCID 5931635312-Bromo-dodec-3-yne

Product 1

HCID 247812561-Dodec-9-ynyl-2-methyl-pyridinium bromideYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

12-Bromo-dodec-3-yne (1 mmol) was added to a solution of 2-picoline (3 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no 2-picoline was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (70%). 1HNMR (300 MHz, CDCl3, ppm), 9.68 (d, 1H), 8.28 (m, 1H), 7.96 (m, 1H), 7.84 (d, 1H), 4.94 (t, 2H), 2.98 (s, 3H), 2.05-2.20 (m, 4H), 1.88-2.00 (m, 2H), 1.20-1.60 (br, 10H), 1.10 (t, 3H).

Workup

  1. temperaturethe solution was refluxed for 24 hours
  2. customThe acetonitrile was removed in vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no 2-picoline
  5. waitwas left in the aqueous layer
  6. extractionThe resulting aqueous solution of the product was extracted with chloroform
  7. customThe chloroform was removed

Sources & evidence

ORD record
ord-10d93db291c348bcaced9de147cb551a
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Reaction notes

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