Potassium Carbonate → 4-(3-Chloro-5-formyl-pyridin-2-yloxy)-benzamide

HRID 130896Notes

Reaction equation

HRID 130896 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[O:10])[CH:5]=[N:6][C:7]=1Cl.[OH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CC(N(C)C)=O>[Cl:1][C:2]1[C:7]([O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=2)=[N:6][CH:5]=[C:4]([CH:9]=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 650524-HydroxybenzamideHCID 115356545,6-Dichloropyridine-3-carbaldehyde

Product 1

HCID 597301934-(3-Chloro-5-formyl-pyridin-2-yloxy)-benzamideYield 51%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

Combine 5,6-dichloro-pyridine-3-carbaldehyde (1.37 g, 7.80 mmol), 4-hydroxy-benzamide (1.18 g, 8.58 mmol), potassium carbonate (1.62 g, 11.7 mmol) in toluene (10 mL) and DMA (30 mL). Stir the reaction mixture at 100° C. for 1 h. Pour the reaction mixture onto H2O (100 mL) and extract with Et2O (100 mL). Wash the organic layer with H2O (2×100 mL), dry the organic phase extracts over magnesium sulfate, filter and concentrate to give the title compound (1.09 g, 51%).

Workup

  1. additionPour the reaction mixture onto H2O (100 mL)
  2. extractionextract with Et2O (100 mL)
  3. washWash the organic layer with H2O (2×100 mL)
  4. dry with materialdry the organic phase extracts over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-366ac34e46294315a635472280c0202e
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

Loading…