Methanol → HCID 20701369, compound

HRID 428134Notes

Reaction equation

HRID 428134 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23]C)[CH2:6][CH2:7][N:8]([CH3:19])[C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.B(Br)(Br)Br.ClCCl.CO>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[OH:23])[CH2:6][CH2:7][N:8]([CH3:19])[C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 9818748Tjn-331HCID 22277759Boron tribromide dichloromethane

Product 1

HCID 20701369HCID 20701369, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-N-(3,4-dimethoxyphenethyl)-N-methyl-3-(3-pyridyl)-2-propenoic acid amide (2.65 g, 8.31 mmol) obtained in Example 84 was dissolved in dichloromethane (66 ml) and 1M boron tribromide-dichloromethane solution (33 ml) was dropwise added under argon at −30° C. and stirred for 14 hours. After methanol was added at the same temperature to stop the reaction, the solvent was distilled out under reduced pressure and hydrogen chloride/methanol solution was added to the residue and heated and refluxed for 1 hour. The solvent was distilled out under reduced pressure and potassium hydroxide/methanol solution was added to the residue to neutralize. The precipitated inorganic salts were filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1) and recrystallized to yield the titled compound (2.19 g, 90%).

Workup

  1. customthe reaction
  2. distillationthe solvent was distilled out under reduced pressure and hydrogen chloride/methanol solution
  3. additionwas added to the residue
  4. temperatureheated
  5. temperaturerefluxed for 1 hour
  6. distillationThe solvent was distilled out under reduced pressure and potassium hydroxide/methanol solution
  7. additionwas added to the residue
  8. filtrationThe precipitated inorganic salts were filtered out
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)
  11. customrecrystallized

Sources & evidence

ORD record
ord-6d34257497f44e0db112a5c6184c70ad
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

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