Dimethylformamide → HCID 18545350, compound

HRID 564863Notes

Reaction equation

HRID 564863 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:8][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 811362-Chloro-3-pyridinol

Product 1

HCID 18545350HCID 18545350, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloro-3-pyridinol (1.3 g), 1.88 g of p-methoxybenzyl chloride, and 1.4 g of potassium carbonate were added to 10 ml of dimethylformamide, followed by stirring at 60° C. for 17 hours. The reaction mixture was diluted with ethyl acetate and washed successively with water and a saturated sodium chloride aqueous solution. After drying, the solvent was removed by evaporation, and the residue was subjected to silica gel column chromatography using a 1:4 (by volume) mixture of ethyl acetate and hexane as a developing solution. The fraction containing the desired compound was concentrated to afford 2.18 g of the title compound.

Workup

  1. washwashed successively with water
  2. customAfter drying
  3. customthe solvent was removed by evaporation
  4. additiona 1:4 (by volume) mixture of ethyl acetate and hexane as a developing solution
  5. additionThe fraction containing the desired compound
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-91c2a399ae384386a6067191474f5271
Source dataset
uspto-grants-2001_01
Patent number
US06169086A

Reaction notes

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