Dimethylamine → 6-(Dimethylamino)pyridine-3-carbonitrile
Reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[CH3:10][NH:11][CH3:12].C(N(CC)CC)C>C(O)C.C1COCC1>[CH3:10][N:11]([CH3:12])[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
In a 25 ml sealed tube, 1.0 g (7.2 mmol) of 6-chloro-nicotino-nitrile and 1.9 ml (10.8 mmol, 5.6 M, 1.5 eq.) of a solution of dimethyl-amine in ethanol are dissolved in 10 ml of THF. Then, 1.5 ml (10.8 mmol, 1.5 eq.) of triethyl-amine are added and the reaction mixture heated to 75° C. After 4 h, the mixture was cooled to rt and concentrated. The residue was taken up in dichloro-methane and aqueous NaHCO3 (5%), the phases separated and the aqueous phases extracted two times with dichloro-methane. The combined organic phases were dried (Na2SO4) and concentrated. The title compound was obtained as a beige solid and used for the next step without further purification. Mass spectrum: m/z (M+H)+: 148.0
Workup
- customIn a 25 ml sealed tube
- temperaturethe mixture was cooled to rt
- concentrationconcentrated
- customaqueous NaHCO3 (5%), the phases separated
- extractionthe aqueous phases extracted two times with dichloro-methane
- dry with materialThe combined organic phases were dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3796503da2d843f7a3c07a7023a8d914
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432293B2
Reaction notes
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