Methylhydrazine → HCID 53402988, compound

HRID 1929758Notes

Reaction equation

HRID 1929758 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][NH:10][NH2:11]>C(OCC)(=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:10]([CH3:9])[NH2:11])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 693532,5-Dibromopyridine

Product 1

HCID 53402988HCID 53402988, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,5-dibromopyridine (500 mg) and methylhydrazine (1 mL) was heated at 100° C. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with a saturated brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. The resultant crude product was purified by column chromatography on silica gel (solvent; chloroform) and the eluted fraction was concentrated. The residue was dissolved in tert-butanol and lyophilized to give 5-bromo-2-(N-methylhydrazino)pyridine (460 mg) as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with a saturated brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant crude product was purified by column chromatography on silica gel (solvent; chloroform)
  6. concentrationthe eluted fraction was concentrated
  7. dissolutionThe residue was dissolved in tert-butanol

Sources & evidence

ORD record
ord-061311aa82cb4213be3f7c1e29bf8470
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

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