4-Methylpyridine → HCID 69779716, compound

HRID 2181779Notes

Reaction equation

HRID 2181779 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[N:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1>C(O)C>[Br-:1].[OH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N+:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 79634-MethylpyridineHCID 779706-Bromo-1-hexanol

Product 1

HCID 69779716HCID 69779716, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Bromo-1-hexanol (27.61 mmol), 4-picoline (30.07 mmol) and absolute ethanol (16 mL) were added to a 3-neck, round-bottomed flask, and were heated at reflux The reaction was stopped after 36 hours. The solvent was removed under vacuum and the residue was washed with diethyl ether (4×100 ml), after which any remaining solvent was removed by vacuum. The product was obtained as an orange-yellow viscous liquid in a 100% yield. 1H NMR (400 MHz, DMSO-d6): δ 9.01 (2H, d, J=6.4 Hz), 8.02 (2H, d, J=6.4 Hz), 4.57 (2H, t, J=7.2 Hz, 7.2 Hz), 4.01 (1H, br), 3.37 (2H, t, J=6.4 Hz, 6.4 Hz), 2.26 (3H, s), 1.89 (2H, p, J=7.2 Hz, 7.2 Hz, 7.2 Hz, 7.2 Hz), 1.21-1.49 (6H, m).

Workup

  1. temperaturewere heated
  2. temperatureat reflux The reaction
  3. customThe solvent was removed under vacuum
  4. washthe residue was washed with diethyl ether (4×100 ml)
  5. customafter which any remaining solvent was removed by vacuum
  6. customThe product was obtained as an orange-yellow viscous liquid in a 100% yield

Sources & evidence

ORD record
ord-013e8d527021490ca250e0b0964a1456
Source dataset
uspto-grants-2005_05
Patent number
US06894169B1

Reaction notes

Loading…