Cesium carbonate → 6-[(3-Nitrophenoxy)methyl]-2-phenylpyridine

HRID 2165924Notes

Reaction equation

HRID 2165924 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.[I-].[K+]>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 111373-NitrophenolHCID 147735482-(Chloromethyl)-6-phenylpyridine

Product 1

HCID 144799796-[(3-Nitrophenoxy)methyl]-2-phenylpyridineYield 101.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 4.2 g (0.03 mol) of 3-nitrophenol in 150 ml of acetone is added 7.5 g (0.05 mol) of 2-chloromethyl-6-phenylpyridine hydrochloride3, 10 g (0.03 mol) of cesium carbonate and 0.5 g of potassium iodide, and the slurry is heated to reflux for 20 hours. The hot mixture is filtered, and the filtrate is concentrated in vacuo to obtain an oil (9.3 g). The crude product is recrystallized from ethyl acetate/pentane to give a first crop (4.5 g, 49%) of crystals, m.p. 77°-80° C. and a second crop (1.7 g, 19%) of crystals, m.p. 77°-81° C.

Workup

  1. temperaturethe slurry is heated
  2. temperatureto reflux for 20 hours
  3. filtrationThe hot mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-7a44208fd18c4a79b18a38b5e19c2e85
Source dataset
uspto-grants-1990_07
Patent number
US04942236

Reaction notes

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