Ammonium Chloride → 6-Tert-butyl-2-methoxynicotinonitrile

HRID 1961486Notes

Reaction equation

HRID 1961486 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7](Cl)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][O-:15].[Na+].[NH4+].[Cl-]>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([O:15][CH3:14])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 532788766-Tert-butyl-2-chloropyridine-3-carbonitrile

Product 1

HCID 667452296-Tert-butyl-2-methoxynicotinonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a screw cap pressure tube, 6-tert-butyl-2-chloronicotinonitrile (410.0 mg, 2.1 mmol) was dissolved in anhydrous MeOH (3.0 ml) under N2. NaOMe (159.3 mg, 2.9 mmol) was added as a solution in anhydrous MeOH (3.0 ml). The tube was sealed and the mixture refluxed for 20 hours. The mixture was allowed to cool. NH4Cl (sat.) was added and the product extracted with EtOAc. The combined organic extracts were washed with water, dried (MgSO4), filtered and concentrated. Purification was done by flash chromatography (Pet. Ether/EtOAc 95:5) to give the title substance in 85% yield.

Workup

  1. customIn a screw cap pressure tube
  2. customThe tube was sealed
  3. temperaturethe mixture refluxed for 20 hours
  4. temperatureto cool
  5. extractionthe product extracted with EtOAc
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification
  11. customto give the title substance in 85% yield

Sources & evidence

ORD record
ord-f7b2f1a063814ccdb56407e82ee6d084
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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