Hydrazine hydrate (1:1) → O-(4-cyano-2-ethoxybenzyl)hydroxyamine

HRID 1294451Notes

Reaction equation

HRID 1294451 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][N:9]2C(=O)C3=CC=CC=C3C2=O)=[C:5]([O:22][CH2:23][CH3:24])[CH:4]=1)#[N:2].O.NN>C(O)C>[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][NH2:9])=[C:5]([O:22][CH2:23][CH3:24])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69431492HCID 69431492, compound

Product 1

HCID 67113324O-(4-cyano-2-ethoxybenzyl)hydroxyamineYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Into a reaction vessel was charged N-(4-cyano-2-ethoxybenzyloxy)phthalimide (17) (27.0 g, 0.084 mol) and ethanol (270 ml), and hydrazine monohydrate (4.6 g, 0.091 mol) were added, and the mixture was stirred for 2 hours at approximately 80° C. The precipitated white solid was removed by filtrated, and the resulted filtrate was subjected to reduce pressure to distill off the solvent. Next, ethyl acetate was added and the mixture was washed with a dilute sodium carbonate aqueous solution, dried over anhydrous magnesium sulfate, then, the solvent was distilled off under reduced pressure, to obtain O-(4-cyano-2-ethoxybenzyl)hydroxyamine (18) (13.4 g, yield from (17) is 83%).

Workup

  1. additionwere added
  2. customThe precipitated white solid was removed
  3. filtrationby filtrated
  4. distillationto distill off the solvent
  5. additionNext, ethyl acetate was added
  6. washthe mixture was washed with a dilute sodium carbonate aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ba3bc732f7e4430da8ce914a90e41e02
Source dataset
uspto-grants-2007_07
Patent number
US07241625B2

Reaction notes

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