Water → 6-Hydrazinyl-2-methylnicotinonitrile

HRID 505694Notes

Reaction equation

HRID 505694 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[N:3]=1.O.[NH2:12][NH2:13].O>C(O)C>[NH:12]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[N:3]=1)[NH2:13]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 123877376-Chloro-2-methylnicotinonitrile

Product 1

HCID 552818556-Hydrazinyl-2-methylnicotinonitrileYield 59.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 6-chloro-2-methylnicotinonitrile (6.2 mmol) in 6.2 mL of ethanol, hydrazine monohydrate (9.3 mmol) was added. The resulting mixture was then heated to 80° C. overnight. The mixture was cooled to room temperature and 2 mL of water was added. It was heated to 80° C. again to a clear solution and then allowed to cool down to room temperature and finally in an ice-bath. The solid was collected by filtration, washed with cold 50% ethanol, and dried under vacuum to give 550 mg of the desired solid product. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.41 (s, 3H), 4.41 (s, 2H), 6.60 (br. s., 1H), 7.66 (d, J=8.59 Hz, 1H), 8.47 (s, 1H); ES-MS m/z 149 (M+H).

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled to room temperature
  3. temperatureIt was heated to 80° C. again to a clear solution
  4. temperatureto cool down to room temperature and finally in an ice-bath
  5. filtrationThe solid was collected by filtration
  6. washwashed with cold 50% ethanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d41e47cedbb14500837b76d06ca08e47
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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