Methanol → HCID 71086657, compound

HRID 538657Notes

Reaction equation

HRID 538657 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10](Cl)[C:11]([C:14]#[N:15])=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].CO.CCCCCC.[C:28](OCC)(=[O:30])C>O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([O:30][CH3:28])[C:11]([C:14]#[N:15])=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 21226206Ethyl acetate hexaneHCID 71086712HCID 71086712, compound2×

Product 1

HCID 71086657HCID 71086657, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL round bottom flask adapted for magnetic stirring and fitted with a reflux condenser and nitrogen inlet is charged 5-(3-fluorophenyl)-3-chloro-2-cyanopyridine, 8, (9.28 g, 40 mmol), sodium methoxide (13.8 mL, 60 mmol) and methanol (200 mL). With stirring, the reaction solution is heated to reflux for 20 hours. The reaction can be determined to be complete due to the disappearance of 5-(3-fluorophenyl)-3-chloro-2-cyanopyridine as measured by TLC analysis using hexane/ethyl acetate (6:3) as the mobile phase and UV 435 nm to visualize the reaction components. The reaction mixture is cooled to room temperature and combined with water (500 mL). The mixture is cooled to 0° C. to 5° C. and stirred for 3 hours. The resulting solid is collected by filtration and washed with water, then hexane. The resulting cake is then dried in vacuo at 40° C. to afford the desired product.

Workup

  1. customTo a 500 mL round bottom flask adapted
  2. customfitted with a reflux condenser and nitrogen inlet
  3. stirringWith stirring
  4. temperaturethe reaction solution is heated
  5. temperatureto reflux for 20 hours
  6. customThe reaction
  7. customthe reaction components
  8. temperatureThe mixture is cooled to 0° C. to 5° C.
  9. stirringstirred for 3 hours
  10. filtrationThe resulting solid is collected by filtration
  11. washwashed with water
  12. customThe resulting cake is then dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-fbed559269ac4411b2613df00bd5efe0
Source dataset
uspto-grants-2014_10
Patent number
US08865748B2

Reaction notes

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