Potassium Carbonate → HCID 86636451, compound

HRID 1483724Notes

Reaction equation

HRID 1483724 reaction equation
Cl[C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[Br:13][C:14]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:15]=1[CH:16]=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.O>[Br:13][C:14]1[CH:21]=[CH:20][C:19]([O:22][C:2]2[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:5]([C:6]#[N:7])=[CH:4][N:3]=2)=[CH:18][C:15]=1[CH:16]=[O:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3871792-Bromo-5-hydroxybenzaldehydeHCID 86636450HCID 86636450, compound

Product 1

HCID 86636451HCID 86636451, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-chloro-4-ethoxy-nicotinonitrile (3.80 g, 20.8 mmol), 2-bromo-5-hydroxy-benzaldehyde (4.60 g, 22.9 mmol) and K2CO3 (4.31 g, 31.2 mmol) in dimethyl formamide (30 mL) was heated to 110° C. for 5 hours. The reaction mixture was diluted with H2O (400 mL) and extracted with ethyl acetate (8×400 mL). The organic extracts were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash column chromatography (15-50% ethyl acetate/hexanes) to give the title compound as a white solid (5.31 g, 73%).

Workup

  1. extractionextracted with ethyl acetate (8×400 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash column chromatography (15-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d851fbe9650842a7b605cd35071da611
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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