Hydrazine hydrate (1:1) → 2-Hydrazinyl-5-Methylpyridine

HRID 1913180Notes

Reaction equation

HRID 1913180 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][N:6]=1>>[NH:2]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][N:6]=1)[NH2:3]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5813932-Chloro-5-methyl-pyridine

Product 1

HCID 41533962-Hydrazinyl-5-Methylpyridine

Procedure

5.7 ml (5.9 g, 117.6 mmol) of hydrazine hydrate are added to 1.0 g (7.8 mmol) of 2-chloro-5-methylpyridine, and the mixture is stirred at boiling point (bath temperature 150° C.) for 16 h. The reaction mixture is cooled and then concentrated on a rotary evaporator, and the residue is co-evaporated three times with in each case 10 ml of ethylene glycol monoethyl ether. The residue is then taken up in dichloromethane, the precipitate is separated off and the filtrate is concentrated under reduced pressure.

Workup

  1. custompoint (bath temperature 150° C.)
  2. customfor 16 h
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated on a rotary evaporator
  5. customthe precipitate is separated off
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f3da5923a1604ed2993cc7b538da3363
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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