Hydrazine hydrate (1:1) → 6-Hydrazinylnicotinonitrile

HRID 601003Notes

Reaction equation

HRID 601003 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.O.[NH2:11][NH2:12]>>[NH:11]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1)[NH2:12]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 5841956-HydrazinylnicotinonitrileYield 46%

Conditions

Temperature
100 °C

Procedure

A mixture of 6-chloro-nicotinonitrile (2.77 g, 20 mmol) and hydrazine hydrate (15 mL) was stirred at 100° C. for 3 h and evaporated. The residue was suspended in ether and filtered, then suspended in sodium bicarbonate solution and filtered, washing with water, and dried to provide 6-hydrazino-nicotinonitrile (1.25 g, 46% yield) as a tan solid. 1H-NMR (DMSO-d6, 500 MHz) 8.59 (s, 1H), 8.35 (s, 1H), 7.74 (d, 1H), 6.75 (s, 1H), 4.44 (s, 2H) ppm; MS (FIA) 135.1 (M+H).

Workup

  1. customevaporated
  2. filtrationfiltered
  3. filtrationfiltered
  4. washwashing with water
  5. customdried

Sources & evidence

ORD record
ord-167f9d56e33149ada71d225e14e8acd2
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

Loading…