Sodium Hydroxide → 2-(5-Aminopyridin-2-yl)-2-methylpropanenitrile

HRID 711356Notes

Reaction equation

HRID 711356 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=1)([CH3:5])[C:3]#[N:4].O.O.Cl[Sn]Cl.[OH-].[Na+]>CCOC(C)=O>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 532174502-Methyl-2-(5-nitropyridin-2-yl)propanenitrile

Product 1

HCID 533931752-(5-Aminopyridin-2-yl)-2-methylpropanenitrileYield 101.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 2-methyl-2-(5-nitropyridin-2-yl)propanenitrile (I-1d, 2 g, 10.4 mmol) and SnCl2.2H2O (9.3 g, 41.6 mmol) in EtOAc (10 mL) was stirred at reflux for 4 h. After cooling to room temperature, aqueous 2 M NaOH (80 mL) was added to adjust the pH to 8˜9, the solid was filtered off, and the filtrate was extracted with ethyl acetate (3×40 mL). The combined organic layers were dried over anhydrous Na2SO4, and concentrated to afford 2-(5-aminopyridin-2-yl)-2-methylpropanenitrile (I-1) (1.7 g, 65.3% yield).

Workup

  1. temperatureat reflux for 4 h
  2. filtrationthe solid was filtered off
  3. extractionthe filtrate was extracted with ethyl acetate (3×40 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-391e8bc7fb854c2fae6dbac7e848dbe8
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

Loading…