Methylhydrazine → Ethyl 2-(1-methylhydrazinyl)acetate

HRID 576874Notes

Reaction equation

HRID 576874 reaction equation
[CH3:1][NH:2][NH2:3].C(N(CC)CC)C.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>ClCCl.C(OCC)(=O)C>[CH3:1][N:2]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH2:3]

Participants

6

Reactant 3

HCID 6061MethylhydrazineHCID 7748Ethyl bromoacetateHCID 8471Triethylamine

Product 1

HCID 20288078Ethyl 2-(1-methylhydrazinyl)acetateYield 77.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methylhydrazine 7.13 ml (150 mmol) and triethylamine 16.7 ml (120 mmol), ethyl 2-bromoacetate 16.7 g (100 mmol) in dichloromethane 50 ml was added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate 300 ml and washed with brine 200 ml. The organic phase was dried over magnesium sulfate and filtered and the mother solution was concentrated in vacuo to obtain the title compound 10.2 g (77%).

Workup

  1. washwashed with brine 200 ml
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe mother solution was concentrated in vacuo

Sources & evidence

ORD record
ord-55b3a420a88f4d3b88cd052751607f87
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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