Methylamine → 5-Chloro-4-methylamino-nicotinonitrile
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
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
- temperatureThe mixture was cooled to room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialthen dried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-d90611d3a6124014bb45ab3784c4e4c1
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855216B2
Reaction notes
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