Methylamine → 5-Chloro-4-methylamino-nicotinonitrile

HRID 2264921Notes

Reaction equation

HRID 2264921 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[Cl:10].[CH3:11][NH2:12]>>[Cl: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 197757134,5-Dichloronicotinonitrile

Product 1

HCID 595965895-Chloro-4-methylamino-nicotinonitrileYield 70%

Conditions

Temperature
60 °C

Procedure

4,5-Dichloronicotinonitrile (500 mg, 2.89 mmol) was suspended in 41% aqueous methylamine solution (5 mL). The resultant mixture was heated, with stirring, up to 60° C. over ca. 30 min. The mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with water, followed by brine then dried (MgSO4) and evaporated to provide the title compound (340 mg, 70%) as a white solid. 1H NMR (CDCl3) 8.39 (1H, s), 8.29 (1H, s), 5.50 (1H, s, br), 3.43 (3H, d, J=5.5 Hz).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialthen dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d90611d3a6124014bb45ab3784c4e4c1
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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