Methylhydrazine → 1-Boc-1-methylhydrazine

HRID 2248109Notes

Reaction equation

HRID 2248109 reaction equation
[C:1]([O:5][C:6]([O:8]C(OC(C)(C)C)=O)=O)([CH3:4])([CH3:3])[CH3:2].[CH3:16][NH:17][NH2:18].[OH-].[Na+]>O1CCCC1.O>[C:1]([O:5][C:6]([N:17]([CH3:16])[NH2:18])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

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

Product 1

HCID 37482801-Boc-1-methylhydrazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Di-t-butyl-dicarbonate (10.91 g, 50 mmole) was added to a solution of methyl hydrazine (2.3 g, 50 mmole) in 100 ml of tetrahydrofuran and 100 ml of water. The pH of the mixture was maintained at 8-9 with 2N sodium hydroxide, and the solution stirred overnight at this pH. The organic solvent was removed in vacuo and the aqueous residue was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and distilled in vacuo to give the title compound as an oil, 3.68g.

Workup

  1. customThe organic solvent was removed in vacuo
  2. extractionthe aqueous residue was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-23f5af3943e6402dbffb624df9bcc366
Source dataset
uspto-grants-1991_08
Patent number
US05037983

Reaction notes

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