Methylamine → 5-Fluoro-4-methylamino-nicotinonitrile

HRID 2264930Notes

Reaction equation

HRID 2264930 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:10].[CH3:11][NH2:12]>>[F:10][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([C:2]=1[NH:12][CH3:11])[C:8]#[N:9]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 595964283-Pyridinecarbonitrile, 4-chloro-5-fluoro-

Product 1

HCID 595965925-Fluoro-4-methylamino-nicotinonitrileYield 70%

Conditions

Temperature
80 °C

Procedure

4-Chloro-5-fluoro-nicotinonitrile (3.5 g, 22.4 mmol) was suspended in 41% aqueous methylamine solution (35 mL). The resultant mixture was heated, with stirring, at 80° C. for 30 minutes. The mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and concentrated in vacuo and the resultant residue triturated in diethyl ether to provide the title compound (2.35 g, 70%) as a white solid. 1H NMR (CDCl3) 8.29 (1H, s), 8.18 (1H, d, J=4.0 Hz), 5.04 (1H, s, br), 3.34 (3H, dd, J=2.2, 5.5 Hz).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customthe resultant residue triturated in diethyl ether

Sources & evidence

ORD record
ord-91b34ee96e904e869a3ae46d26be4c4c
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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