Hydroxyamine hydrochloride → HCID 136343617, compound

HRID 1251159Notes

Reaction equation

HRID 1251159 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[CH:17]=O)=[CH:5][CH:4]=1.Cl.[NH2:20][OH:21].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[CH:17]=[N:20][OH:21])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 22503577HCID 22503577, compound

Product 1

HCID 136343617HCID 136343617, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3-(4-Methoxyphenylethynyl)-4-pyridinecarboxaldehyde (4.965 g) was dissolved in ethanol (70 ml), a solution of hydroxylamine hydrochloride (2.179 g) and sodium acetate (3.429 g) in water (18 ml) was added thereto, and then the mixture was stirred at 70° C. overnight. After cooling as it was, the reaction mixture was evaporated and partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow solid (4.724 g, yield; 96%).

Workup

  1. temperatureAfter cooling as it
  2. customthe reaction mixture was evaporated
  3. custompartitioned between ethyl acetate and water
  4. washThe resulting organic layer was washed with water
  5. dry with materialdried (over MgSO4)
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-bbef382e794c46a99828310fdb736aa3
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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