Diethyl Ether → 4-(Methylamino)pyridine-3-carbonitrile

HRID 2264896Notes

Reaction equation

HRID 2264896 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.C(OCC)C.[CH3:15][NH2:16]>O>[CH3:15][NH:16][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6329MethylamineHCID 134111124-Chloro-nicotinonitrile

Product 1

HCID 553005854-(Methylamino)pyridine-3-carbonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4-Chloronicotinonitrile (45.0 g, 324 mmol) was suspended in water (250 mL) and 41% aqueous methylamine solution (250 mL). The resultant mixture was heated, with stirring, at 90° C. for 1 hour before the mixture was cooled to room temperature and extracted with ethyl acetate (×2). The combined organic layers were washed with water, followed by brine then dried (MgSO4) and evaporated to provide a residue. Trituration of the residue with diethyl ether gave the title compound (40.4 g, 93%) as a white solid. 1H NMR (CDCl3) 2.98 (3H, d, J=5.1 Hz), 5.20 (1H, br s), 6.53 (1H, d, J=6.13 Hz), 8.35 (1H, d, J=6.13 Hz), 8.43 (1H, s).

Workup

  1. temperaturewas cooled to room temperature
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with water
  4. dry with materialthen dried (MgSO4)
  5. customevaporated
  6. customto provide a residue

Sources & evidence

ORD record
ord-9f9fb2abfbd648179b6ca93ed1bcdc61
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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