Pyridine → 2-Aminoisonicotinonitrile

HRID 887650Notes

Reaction equation

HRID 887650 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].[N:15]1C=CC=CC=1>C(Cl)Cl>[NH2:15][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]#[N:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 70155242-Aminoisonicotinonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a slurry of 2-chloro-4-cyanopyridine (10.00 g, 0.079 mol) and sodiumbicarbonate (19.92 g, 0.237 mol) in amine (0.174 mol) was added pyridine (35.0 mL) and the reaction was heated to 90° C. for 3 h. The reaction was then cooled to RT, diluted with the addition of CH2Cl2 (100 mL) and filtered. The solid was washed with EtOAc. Combined washes were concentrated in vacuo. A mixture of MeOH/hexanes was added and kept in the fridge for 12 h. The crystals that formed were filtered and washed with hexanes.

Workup

  1. temperatureThe reaction was then cooled to RT
  2. filtrationfiltered
  3. washThe solid was washed with EtOAc
  4. concentrationwere concentrated in vacuo
  5. additionA mixture of MeOH/hexanes
  6. additionwas added
  7. customThe crystals that formed
  8. filtrationwere filtered
  9. washwashed with hexanes

Sources & evidence

ORD record
ord-bd573872405042bf86ebdf8a971883c2
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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