3-Methyl-5-nitropicolinonitrile → 5-Amino-3-methylpyridine-2-carbonitrile

HRID 515781Notes

Reaction equation

HRID 515781 reaction equation
[CH3:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[H][H]>CO.[Pd]>[NH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([C:11]#[N:12])=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 124040403-Methyl-5-nitropicolinonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 218645665-Amino-3-methylpyridine-2-carbonitrileYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-methyl-5-nitropicolinonitrile (2.9 g, 17.8 mmol) and Pd/C (cat.) in MeOH (60 mL) was hydrogenated overnight with a balloon of hydrogen. Pd/C was removed through a pad of celite and the filtrate was evaporated to dryness to afford 2.2 g of 5-amino-3-methylpicolinonitrile as a greenish solid. 1H NMR (300 MHz, DMSO-d6) δ 7.83 (s, 1H), 6.79 (s, 1H), 6.32 (s, 2H), 2.29 (s, 3H).

Workup

  1. customPd/C was removed through a pad of celite
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-2a048f3e4e0b4249b5dbec1cf6a35d3e
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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