4'-Chloro-2,2':6',2''-terpyridine → 4-Ethoxy-2,6-dipyridin-2-ylpyridine

HRID 273304

Reaction equation

HRID 273304 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:3]=1.[CH2:20]([O-:22])[CH3:21].[Na+]>O>[CH2:20]([O:22][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:3]=1)[CH3:21]

Participants

4

Reactant 2

HCID 6677484'-Chloro-2,2':6',2''-terpyridineHCID 2723922Sodium ethoxide

Product 1

HCID 98731094-Ethoxy-2,6-dipyridin-2-ylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere, 900 mg (3.4 mmol) of 4′-chloro-[2,2′;6′,2″]terpyridine are added to 15 ml of a 0.7M ethanolic sodium ethanolate solution. The mixture is heated at reflux for 20 hours. The mixture is allowed to cool and 20 ml of water are added, and 4′-ethoxy-[2,2′;6′,2″]terpyridine is filtered off in the form of a white solid. 1H-NMR (360 MHz, DMSO-d6): 1.40 (t, 3H, 6.8 Hz); 4.28 (q, 2H, 6.8 Hz); 7.42-7.53 (m, 2H); 7.93 (s, 2H); 7.95-8.02 (m, 2H); 8.58 (d, 2H, J=8.1 Hz); 8.69 (d, 2H, J=4 Hz).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 20 hours
  3. temperatureto cool
  4. filtration4′-ethoxy-[2,2′;6′,2″]terpyridine is filtered off in the form of a white solid

Sources & evidence

ORD record
ord-959678103e89408e8f1cd36231f41f18
Source dataset
uspto-grants-2008_11
Patent number
US07456285B2

Linked notes

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