Hydrazine hydrate (1:1) → (3-methoxybenzyl)hydrazine

HRID 1596400Notes

Reaction equation

HRID 1596400 reaction equation
O.[NH2:2][NH2:3].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9]Cl>C(O)C>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][NH:2][NH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 699943-Methoxybenzyl chloride

Product 1

HCID 2760980(3-methoxybenzyl)hydrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

While a solution of hydrazine monohydrate (10 g, 0.2 mol) in ethanol (35 ml) was heated under reflux, a solution of 3-methoxybenzyl chloride (5.0 g, 32 m mol) in ethanol (15 ml) was added drop-wise thereto over a period of 30 minutes. After this mixture was further refluxed for 2 hours, the solvent was distilled off under reduced pressure. The oily residue was extracted with ether (2×30 ml). After the extract was dried, the solvent was distilled off under reduced pressure. The resulting residue was subjected to chromatography on silica gel (40 g) using chloroform-methanol (20:1), so that there was obtained a crude fraction containing the desired compound. Then, this crude fraction was distilled (120-123° C./1-2 mmHg) to obtain the desired compound (2.9 g, 60%) as a colorless oily material.

Workup

  1. temperatureunder reflux
  2. temperatureAfter this mixture was further refluxed for 2 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionThe oily residue was extracted with ether (2×30 ml)
  5. customAfter the extract was dried
  6. distillationthe solvent was distilled off under reduced pressure
  7. customso that there was obtained a crude fraction

Sources & evidence

ORD record
ord-fa811121e290411dbedeed40a2932f89
Source dataset
uspto-grants-2001_09
Patent number
US06291485B1

Reaction notes

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