Methylamine → HCID 9855809, compound

HRID 2064305Notes

Reaction equation

HRID 2064305 reaction equation
C1(C)C=CC(S(O[CH:11]([CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][CH:19]=[C:20]([O:22][CH3:23])[CH:21]=2)[CH3:12])(=O)=O)=CC=1.[CH3:25][NH2:26]>C(O)C>[CH3:25][NH:26][CH:11]([CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:17]=[N:18][CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[CH3:12]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 87467528HCID 87467528, compound

Product 1

HCID 9855809HCID 9855809, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (4E)-5-(5-methoxy-3-pyridyl)-4-penten-2-ol p-toluenesulfonate (5.00 g, 14.41 mmol), methylamine (150 mL, 40% solution in water), and ethyl alcohol (10 mL) was stirred at ambient temperature for 18 h. The resulting solution was extracted with chloroform (3×100 mL). The combined chloroform extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography over aluminum oxide, eluting with ethyl acetate-methanol (7:3, v/v). Selected fractions were combined and concentrated by rotary evaporation, producing an oil. Further purification by vacuum distillation furnished 1.25 g (41.8%) of a colorless oil, by 90-100° C. at 0.5 mm Hg.

Workup

  1. extractionThe resulting solution was extracted with chloroform (3×100 mL)
  2. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude product was purified by column chromatography over aluminum oxide
  6. washeluting with ethyl acetate-methanol (7:3
  7. concentrationconcentrated by rotary evaporation
  8. customproducing an oil
  9. customFurther purification
  10. distillationby vacuum distillation

Sources & evidence

ORD record
ord-6b8b0bbac0da4e4b8cc045df17a8fc5f
Source dataset
uspto-grants-2012_10
Patent number
US08288420B2

Reaction notes

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