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

HRID 859741Notes

Reaction equation

HRID 859741 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-06603e9ea18d488090fbca4df3932b3d
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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