2-Methylpyridine → HCID 24742486, compound

HRID 1925442Notes

Reaction equation

HRID 1925442 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13]Br.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]>C(#N)C>[Br-:1].[Br-:1].[CH2:2]([N+:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][N+:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

4

Reactant 2

HCID 79752-MethylpyridineHCID 58338516HCID 58338516, compound

Product 1

HCID 24742486HCID 24742486, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

cis-cis-1,12-Dibromo-dodeca-5,7-diene was added to a solution of 2-picoline (3 mmol) in acetonitrile and the solution 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 picoline left in the aqueous layer. The resulting aqueous solution of the product was lyophilized to yield the pure product. (76%). 1HNMR (300 MHz, D2O, ppm) 8.52 (dd, J=6.3, 2H), 8.17 (dt, J=7.8, J=1.5, 2H), 7.72 (d, J=7.8, 2H), 7.64 (t, J=6.3, 2H), 6.18-6.23 (m, 2H), 5.33-5.41 (m, 2H), 4.37 (t, J=7.1, 4H), 2.66 (s, 6H), 2.09 (q, J=7.5, 4H), 1.72-1.82 (m, 4H), 1.36 (p, J=7.5, 4H). 13CNMR, 155.26, 145.01, 144.73, 132.25, 130.23, 125.64, 124.15, 58.06, 29.10, 26.38, 25.61, 19.73.

Workup

  1. temperaturethe solution 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 picoline
  5. waitleft in the aqueous layer
  6. customto yield the pure product

Sources & evidence

ORD record
ord-8489ce6960724245ae0833d81d1aab81
Source dataset
uspto-grants-2012_05
Patent number
US08178678B2

Reaction notes

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