Hydrazine → 6-Hydrazinylnicotinonitrile

HRID 1925108Notes

Reaction equation

HRID 1925108 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[NH2:10][NH2:11]>CCO>[NH:10]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1)[NH2:11]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 5841956-HydrazinylnicotinonitrileYield 51.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspended mixture of 6-chloronicotinonitrile (7 g, 50.8 mmol) in EtOH (50 mL), was added NH2NH2 (10 g, 310.2 mmol). The mixture was stirred at room temperature for 10 min, and then 60° C. for 5 h. The mixture was cooled to room temperature. The solids were filtered out, washed with water and dried under high vacuum to give 6-hydrazinylnicotinonitrile (3.5 g). Compound 6 was prepared from 6-hydrazinylnicotinonitrile following the procedure of the synthesis of compound 4. 1H NMR (400 MHz, CDCl3-CD3OD 10:1) δ ppm 11.37 (s, 1H), 8.70 (t, J=1.2 Hz, 1 H), 8.14 (s, 1 H), 8.11(dd, J=1.04 and 9.52 Hz, 1 H), 7.96 (dd, J=1.12 and 9.52 Hz, 1 H), 7.61 (dd, J=1.52 and 9.48 Hz, 1 H), 7.38 (d, J=9.0 Hz, 1 H), 1.77 (m, 1 H), 1.06 (m, 2 H), 0.90 (m, 2H) ESI-MS:m/z 377.2 (M+H)+.

Workup

  1. wait60° C. for 5 h
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe solids were filtered out
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-efd29034311b40b691d3e530c86e7115
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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