Sulfuric acid magnesium salt (1:1) → N-[3-(3-Methoxyphenyl)propylidene]-N'-(4-pyridinyl)hydrazine hydrochloride

HRID 612453

Reaction equation

HRID 612453 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH:11]=O)[CH:6]=[CH:7][CH:8]=1.[ClH:13].[NH:14]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[NH2:15].S([O-])([O-])(=O)=O.[Mg+2]>C(O)C>[ClH:13].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH:11]=[N:15][NH:14][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 114237693-(3-Methoxyphenyl)propionaldehydeHCID 223202584-Hydrazinylpyridine hydrochloride

Product 1

HCID 70107610N-[3-(3-Methoxyphenyl)propylidene]-N'-(4-pyridinyl)hydrazine hydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of 3-(3-methoxyphenyl)propionaldehyde (6.46 g), 4-hydrazinopyridine hydrochloride (6.30 g) and magnesium sulfate (5 g) in ethanol (75 ml) was heated under reflux, under nitrogen, with stirring, for 45 mins. The reaction mixture was filtered, the filter cake was washed with ethyl acetate, and the filtrate was concentrated in vacuo. The residue was triturated with ethyl acetate to give 7 g (61%) of product, mp 155-156° C.

Workup

  1. temperatureunder reflux, under nitrogen
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was washed with ethyl acetate
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-94ca095354cf45b59cf18d606a9ab0bc
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Linked notes

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