Ammonia → 2-Amino-6-methylpyridine-3-carbonitrile

HRID 605043

Reaction equation

HRID 605043 reaction equation
Cl[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH3:11]>C(O)C>[NH2:11][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 5204002-Chloro-6-methylpyridine-3-carbonitrile

Product 1

HCID 130271112-Amino-6-methylpyridine-3-carbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-6-methyl-nicotinonitrile (25 g, 0.164 mol) and liquid ammonia (250 mL) in 500 mL of ethanol were reacted in a sealed high-pressure vessel at 130° C. for 20 hours. The reaction mixture was concentrated under vacuum and the residue washed with water (2×50 mL) then dried in a vacuum oven for 24 hours to provide the title compound as a light yellow solid (18 g, 82%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.30 (s, 3H), 6.52 (d, J=7.7 Hz, 1H), 6.78 (s, 2H), 7.73 (d, J=7.7 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. washthe residue washed with water (2×50 mL)
  3. customthen dried in a vacuum oven for 24 hours

Sources & evidence

ORD record
ord-22f55687e3a948fba525e56a5a5183c4
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Linked notes

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