Water → HCID 23092614, compound

HRID 1616526Notes

Reaction equation

HRID 1616526 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])O.[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20]Cl)=[C:16]([C:22]#[N:23])[N:15]=1.O>C(#N)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:16]([C:22]#[N:23])[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 516892Sodium BicarbonateHCID 23092607HCID 23092607, compound

Product 1

HCID 23092614HCID 23092614, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution (10 ml) of 1.50 g (5.70 mmol) of the resulting N-oxide substance in phosphorus oxychloride was stirred at 80° C. for 1 hour. The reaction solution was concentrated in vacuo, a saturated aqueous solution of sodium hydrogen carbonate was added to the residue followed by extracting with chloroform and the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous saline solution. After drying and concentrating, the resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=2:1) to give 625 mg (yield: 58%) of 2-chloro-5-chloromethyl-6-cyanopyridine as a white solid. Phenol (30 mg; 0.32 mmol) and 44 mg (0.32 mmol) of sodium hydrogen carbonate were added to a solution (5 ml) of 50 mg (0.27 mmol) of 2-chloro-5-chloromethyl-6-cyanopyridine in acetonitrile followed by stirring at room temperature for 8 hours and 30 minutes. Water was added to the reaction solution followed by extracting with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution, dried and concentrated in vacuo and the resulting residue was purified by a thin-layer column chromatography (hexane:ethyl acetate=6:1) to give 61 mg (yield: 93%) of 2-chloro-6-cyano-5-phenoxymethylpyridine as a white solid.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous saline solution
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customthe resulting residue was purified by a thin-layer column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-1a0876f2a90d4939ad31561236310e41
Source dataset
uspto-grants-2014_07
Patent number
US08765789B2

Reaction notes

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