Methylhydrazine → N',6-dimethylpyridine-2-carbohydrazonamide

HRID 2387132Notes

Reaction equation

HRID 2387132 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][NH:11][NH2:12]>C(O)C>[CH3:10][NH:11][N:12]=[C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)[NH2:9]

Participants

4

Reactant 2

HCID 6061Methylhydrazine2×HCID 741826-Methylpyridine-2-carbonitrile

Product 1

HCID 69057285N',6-dimethylpyridine-2-carbohydrazonamideYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Methylpyridine-2-carbonitrile (45.3 g, 0.384 mol) and methylhydrazine (94 mL, 5.30 mol) were mixed with ethanol (200 mL). The mixture was stirred at room temperature overnight, and then an additional portion (18 mL, 1.00 mol) of methylhydrazine was added, and the mixture was stirred for a further 16 h. The mixture was then evaporated to give 58.0 g of crude N′,6-dimethylpyridine-2-carbohydrazonamide (˜92% yield), which was used for the next stage of the synthesis without additional purification.

Workup

  1. stirringthe mixture was stirred for a further 16 h
  2. customThe mixture was then evaporated

Sources & evidence

ORD record
ord-54bbde3b792d487eb843e14431affa0d
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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