Benzyl Chloride → HCID 86723689, compound

HRID 577457Notes

Reaction equation

HRID 577457 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[C:11]#[N:12])[CH3:2].Cl[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.[Ag-]=O>[CH2:14]([O:10][C:5]1[C:4]([C:11]#[N:12])=[C:3]([CH2:1][CH3:2])[CH:8]=[C:7]([CH3:9])[N:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 7503Benzyl ChlorideHCID 156418004-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 86723689HCID 86723689, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (Cpd AA, 1.1 g, 6.8 mmol), (chloromethyl)benzene (1.1 mL, 9.4 mmol, 1.4 equiv) and silver(I) oxide (1.8 g, 7.7 mmol) in anhydrous toluene (22.7 mL) was heated at 110° C. for 17 hours. The reaction mixture was cooled to 23° C. then filtered through CELITE®. The filtrate was concentrated under vacuum. The residue was purified by column chromatography (heptane/EtOAc) to give 2-(benzyloxy)-4-ethyl-6-methylpyridine-3-carbonitrile (Cpd BB, 1.42 g, 83%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to 23° C.
  2. filtrationthen filtered through CELITE®
  3. concentrationThe filtrate was concentrated under vacuum
  4. customThe residue was purified by column chromatography (heptane/EtOAc)

Sources & evidence

ORD record
ord-45fbec9cd137473fb3784c556afecee3
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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