Methylhydrazine → 1-Boc-1-methylhydrazine

HRID 1461881Notes

Reaction equation

HRID 1461881 reaction equation
[CH3:1][NH:2][NH2:3].[CH3:4][C:5]([O:8][C:9]([O:11]C(OC(C)(C)C)=O)=O)([CH3:7])[CH3:6].[OH-].[Na+]>O1CCCC1.O>[CH3:4][C:5]([CH3:7])([O:8][C:9]([N:2]([CH3:1])[NH2:3])=[O:11])[CH3:6]

Participants

6

Reactant 3

HCID 6061MethylhydrazineHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 37482801-Boc-1-methylhydrazineYield 50.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of methylhydrazine (2.3 g, 50 mmole) in 100 ml of tetrahydrofuran and 100 ml of water was treated with BOC anhydride (10.91 g, 50 mmole) at 20° C. and the pH was maintained at 8-9 with the dropwise addition of 2N sodium hydroxide. After the pH stabilized, the solution was stirred overnight at 20° C. and pH 8-9. The organic solvent was evaporated in vacuo and the residue was extracted with ethyl acetate. The organic solution was washed with water, dried over sodium sulfate and evaporated. The residual oil was flash-distilled in vacuo to give 3.68 g of the title compound as a colorless oil.

Workup

  1. customThe organic solvent was evaporated in vacuo
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. distillationThe residual oil was flash-distilled in vacuo

Sources & evidence

ORD record
ord-5fd7042f7c374fc68f322a612c912e71
Source dataset
uspto-grants-1991_12
Patent number
US05077432

Reaction notes

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