Hydrazine hydrate (1:1) → 1-(2-Hydrazinopyridin-4-yl)ethanol

HRID 1845865Notes

Reaction equation

HRID 1845865 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>CO.CCOCC>[NH:12]([C:2]1[CH:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=1)[NH2:13]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 140536542-Chloro-alpha-methyl-4-pyridinemethanol

Product 1

HCID 672564351-(2-Hydrazinopyridin-4-yl)ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

1-(2-chloropyridin-4-yl)ethanol (5d) (14.3 g) was dissolved in hydrazine hydrate (275 mL). The resulting mixture was heated at 100° C. with stirring overnight. The mixture was concentrated under vacuum to give a yellow oil that was dissolved in a small volume of methanol and ether was added, which resulted in precipitation of a white solid. The obtained suspension was stirred for 30 minutes and filtered, and the residue (hydrazine hydrochloride) was discarded. The filtrate was concentrated under vacuum to give the title compound (13.7 g) as a light-brown oil.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customto give a yellow oil that
  3. additionwas added
  4. customwhich resulted in precipitation of a white solid
  5. stirringThe obtained suspension was stirred for 30 minutes
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-f10144315593443384fb8eac4ba5b9ee
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

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