Hydrazine hydrate (1:1) → tert-Butyl (aminooxy)acetate

HRID 414866Notes

Reaction equation

HRID 414866 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]1C(=O)C2=CC=CC=C2C1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>ClCCl>[C:1]([O:5][C:6]([CH2:8][O:9][NH2:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 12919120Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate

Product 1

HCID 12919121tert-Butyl (aminooxy)acetateYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 1.35 l of dichloromethane is dissolved 37.4 g (0.135 mole) of N-(tert-butoxycarbonylmethoxy) phthalimide, and 9.21 ml (0.189 mole) of hydrazine hydrate is added dropwise to the solution over the period of 10 minutes, followed by stirring at room temperature for 2 hours. 3.95 ml (0.081 mole) of hydrazine hydrate is furthermore added, followed by stirring for further 1.5 hours. The reaction solution is filtered, and the filtrate is washed with 300 ml of 2N ammonium water and aqueous sodium chloride solution successively, and dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure to give 18.95 g (95.4%) of O-(tert-butoxycarbonylmethyl)hydroxylamine as a yellow oily product.

Workup

  1. additionis added dropwise to the solution over the period of 10 minutes
  2. stirringby stirring for further 1.5 hours
  3. filtrationThe reaction solution is filtered
  4. washthe filtrate is washed with 300 ml of 2N ammonium water and aqueous sodium chloride solution successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-9aa65a6bfbf94f5d90510cbef3e8d95b
Source dataset
uspto-grants-1988_12
Patent number
US04794108

Reaction notes

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