Potassium Carbonate → 2-Chloro-5-((4-methoxybenzyl)oxy)-3-methylpyridine

HRID 930487Notes

Reaction equation

HRID 930487 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].Cl[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([O:8][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 128520156-Chloro-5-methylpyridin-3-ol

Product 1

HCID 867322892-Chloro-5-((4-methoxybenzyl)oxy)-3-methylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-chloro-5-methylpyridin-3-ol (250 mg, 0.0017 mol), 1-(chloromethyl)-4-methoxybenzene (0.328 g, 0.0020 mol, Sigma Aldrich), and potassium carbonate (0.482 g, 0.0034 mol) in DMF (5 mL) was allowed to stir for 3 h at 60° C. After completion of the reaction, reaction mixture was cooled to ambient temperature and poured into ice cold water (25 mL). The obtained solid was filtered, washed with water (2×10 mL) and dried to obtain 2-chloro-5-((4-methoxybenzyl)oxy)-3-methylpyridine as an off white solid (400 mg, 87%).

Workup

  1. customAfter completion of the reaction, reaction mixture
  2. temperaturewas cooled to ambient temperature
  3. filtrationThe obtained solid was filtered
  4. washwashed with water (2×10 mL)
  5. customdried

Sources & evidence

ORD record
ord-c9c95c0e9d4a4e11ac30e65ef67d3682
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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