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

HRID 2361939Notes

Reaction equation

HRID 2361939 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].O.NN>CO.O1CCCC1>[NH2:3][O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

4

Reactant 2

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

Product 1

HCID 12919121tert-Butyl (aminooxy)acetateYield 87%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate (Compound XXIII-1) (13.86 g, 50 mmol) in methanol:tetrahydrofuran (2:3, 150 ml) was added hydrazine monohydrate (7.28 ml, 150 mmol) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (300 ml) and the mixture was washed with sat. NaHCO3 aq. (300 ml). The organic layer was washed with brine (300 ml), dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to obtain the title compound (6.40 g, 87%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate (300 ml)
  3. washthe mixture was washed with sat. NaHCO3 aq. (300 ml)
  4. washThe organic layer was washed with brine (300 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ec397da5f46f4375aa262595b14d18ee
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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