Sodium Hydroxide → HCID 22240328, compound

HRID 891964Notes

Reaction equation

HRID 891964 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[CH2:18][C:19]#[N:20].[OH-].[Na+]>C(O)C>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[C:18]1[C:19]([NH2:20])=[N:1][C:2]2[C:7]([CH:8]=1)=[CH:6][N:5]=[CH:4][CH:3]=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76678(2,6-Dichlorophenyl)acetonitrileHCID 27610334-Aminonicotinaldehyde

Product 1

HCID 22240328HCID 22240328, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

4-Aminonicotinaldehyde (100 mg, 0.78 millimole (hereinafter “mmol”)), 2,6-dichlorophenylacetonitrile (217 mg, 1.2 mmol), 10% aqueous NaOH (0.101 mL, 0.25 mmol) and 700 uL of absolute ethanol are combined and heated at 65° C. for 24 hours (hereinafter “h”). The reaction mixture is cooled to ambient temperature and the solvents are evaporated under reduced pressure. The residue is diluted with 700 uL of DMSO filtered and purified with preparative reverse phase chromatography to afford the title compound as a yellow solid (191 mg, 84% yield). MS ES+ m/z=290.

Workup

  1. temperatureThe reaction mixture is cooled to ambient temperature
  2. customthe solvents are evaporated under reduced pressure
  3. additionThe residue is diluted with 700 uL of DMSO
  4. filtrationfiltered
  5. custompurified with preparative reverse phase chromatography

Sources & evidence

ORD record
ord-4d0b2680644e47faabe84f4839a8f0e0
Source dataset
uspto-grants-2006_02
Patent number
US07005434B2

Reaction notes

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