Ammonia → 1-[6-tert-Butylpyridin-3-yl]propan-1-one

HRID 1438402Notes

Reaction equation

HRID 1438402 reaction equation
S(=O)(=O)(O)O.[C:6]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)(=[O:9])[CH2:7][CH3:8].[CH3:16][C:17](C)([CH3:21])[C:18](O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].N>O.[N+]([O-])([O-])=O.[Ag+]>[C:17]([C:13]1[N:12]=[CH:11][C:10]([C:6](=[O:9])[CH2:7][CH3:8])=[CH:15][CH:14]=1)([CH3:21])([CH3:18])[CH3:16]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 6417Pivalic acidHCID 62648Ammonium PersulfateHCID 740741-(3-Pyridyl)propan-1-one

Product 1

HCID 670470641-[6-tert-Butylpyridin-3-yl]propan-1-oneYield 98%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a 10% sulphuric acid aqueous solution (22 ml) of 3-propionylpyridine (Lancaster, 2.70 g, 20 mmol), trimethylacetic acid (10.21 g, 0.1 mol), silver nitrate (0.68 g, 4 mmol) and ammonium persulfate in water (36 ml) were added and the mixture was stirred for 1.5 hours at 70° C. Then, the mixture was basified with 25% ammonia solution (pH=9˜10) and extracted with DCM. The organic layer was washed with brine and dried over sodium sulfate. Removal of the solvent gave a residue, which was purified by column chromatography, eluting with hexane/EtOAc (5:1), to give the title compound (3.75 g, 98%) as a yellow oil.

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvent
  5. customgave a residue, which
  6. customwas purified by column chromatography
  7. washeluting with hexane/EtOAc (5:1)

Sources & evidence

ORD record
ord-1871b26445844201a63ce81798f0a567
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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