Potassium Carbonate → 2,4-Dimethyl-6-[2-(4-nitro-phenoxy)-ethoxy]-pyridine

HRID 37842Notes

Reaction equation

HRID 37842 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1>CN(C=O)C>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([O:1][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2359871-(2-Bromoethoxy)-4-nitrobenzeneHCID 178426542HCID 178426542, compound

Product 1

HCID 668510252,4-Dimethyl-6-[2-(4-nitro-phenoxy)-ethoxy]-pyridineYield 13.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-hydroxy-4,6-dimethylpyridine (1.7 g, 13.8 mmol), potassium carbonate (3.82 g, 27.6 mmol) and 1-(2-bromo-ethoxy)-4-nitro-benzene (4.0 g, 16.6 mmol) in DMF (30 mL) was heated to 120° C. and maintained for 15 h. The mixture was cooled to ambient temperature, filtered and concentrated to give a residue which was purified by column chromatography using 4% ethyl acetate/petroleum ether as eluent to afford 2,4-dimethyl-6-[2-(4-nitro-phenoxy)-ethoxy]-pyridine as yellow solid (530 mg, 11%).

Workup

  1. temperaturemaintained for 15 h
  2. temperatureThe mixture was cooled to ambient temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e5cab483bc94455fb4e325c1e2f202a0
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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