Potassium Carbonate → HCID 67606024, compound

HRID 1024679Notes

Reaction equation

HRID 1024679 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14](Cl)=[N:13][C:12]=1Cl)[CH3:8].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1>CN(C=O)C>[CH2:7]([O:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([O:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)=[N:13][C:12]=1[O:4][C:1]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 12263987Ethyl 2,6-dichloronicotinate

Product 1

HCID 67606024HCID 67606024, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Potassium carbonate 1.58 g (11.5 mmol) was added to a stirred solution of 2,6-dichloro-nicotinic acid ethyl ester 1.0 g (4.6 mmol) in 5 ml of DMF and stirred for 10 min. 4-Hydroxy-benzonitrile 1.36 g (11.5 mmol), dissolved in 5 ml of DMF, was added dropwise to the stirred DMF solution and the flask was stirred at 80° C. for 4 h. The reaction mixture was poured into ice-cold water and the result was partitioned using ethyl acetate. The organic phase was washed with 1 M of Na2CO3 and saturated brine solution, dried over sodium sulphate and concentrated. The oily residue was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 1.6 g of the required product. Percentage purity: 84.8%, (M+1)=385.1. 1H NMR (DMSO-d6): 1.36 (3H, t), 4.22 (214, q), 6.78 (1H, d), 7.06 (4H, d), 7.58 (4H, d), 8.21 (1H, d).

Workup

  1. stirringthe flask was stirred at 80° C. for 4 h
  2. additionThe reaction mixture was poured into ice-cold water
  3. customthe result was partitioned
  4. washThe organic phase was washed with 1 M of Na2CO3 and saturated brine solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe oily residue was purified by column chromatography

Sources & evidence

ORD record
ord-ae81d33b700b40ad84260f317308e1f2
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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