Water → HCID 351532, compound

HRID 1352514Notes

Reaction equation

HRID 1352514 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Cl.[NH2:13][OH:14].C([O-])(=O)C.[Na+].O>C(O)C>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:13][OH:14])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74794-(Dimethylamino)BenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 351532HCID 351532, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(dimethylamino)benzaldehyde (5.0 g), hydroxylamine hydrochloride (2.3 g), and sodium acetate (2.7 g) in ethanol (61 mL)/water (11 mL) is heated at reflux temperature for 1 hour. The mixture is cooled to ambient temperature and partitioned between diethyl ether and water. The aqueous layer is back-extracted with diethyl ether and the combined organic extracts are washed with saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2.6 g pure white solid as the product. MS: m/z 165 (M+H)+.

Workup

  1. temperatureat reflux temperature for 1 hour
  2. custompartitioned between diethyl ether and water
  3. extractionThe aqueous layer is back-extracted with diethyl ether
  4. washthe combined organic extracts are washed with saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4bde9484d844792a704c8b579093d76
Source dataset
uspto-grants-2007_05
Patent number
US07220768B2

Reaction notes

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