Hydrazine hydrate (1:1) → (6-Hydrazinopyridin-3-yl)methanol

HRID 1526073Notes

Reaction equation

HRID 1526073 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.O.[NH2:11][NH2:12]>>[NH:11]([C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1)[NH2:12]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 177161(6-Chloropyridin-3-yl)methanol

Product 1

HCID 59186956(6-Hydrazinopyridin-3-yl)methanol

Procedure

20.0 g (139 mmol) (6-chloropyridin-3-yl)methanol are heated under reflux overnight in 400 ml of a 35% strength aqueous hydrazine hydrate solution. The mixture is concentrated, toluene is added, the mixture is concentrated again and the residue is stirred with a mixture of methylene chloride, methanol and diethyl ether. The crystalline residue (hydrazine hydrochloride) is filtered off, the filtrate is concentrated and the residue is dried in vacuo.

Workup

  1. concentrationThe mixture is concentrated
  2. additiontoluene is added
  3. concentrationthe mixture is concentrated again
  4. filtrationThe crystalline residue (hydrazine hydrochloride) is filtered off
  5. concentrationthe filtrate is concentrated
  6. customthe residue is dried in vacuo

Sources & evidence

ORD record
ord-a4f9d135ea154b78bbad1a82ddbdd6ec
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

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