Application of 2-methylpyridine-4-carbonitrile_Industrial additives

Application background and overview of 2-methylpyridine-4-carbonitrile

2-Methylpyridine-4-carbonitrile can be used as a pharmaceutical synthesis intermediate. If 2-methylpyridine-4-carbonitrile is inhaled, move the patient to fresh air; if skin contact occurs, take off contaminated clothing and rinse the skin thoroughly with soap and water, if there is discomfort with basic copper carbonate , seek medical attention; if eye contact occurs, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.

Application and preparation of 2-methylpyridine-4-carbonitrile

Preparation of compound 2-methylpyridine-4-carbonitrile: Compound 1-1 (5.0g, 36.1mmol), trimethylaluminum n-hexane solution (36.1ml, 2N), tetrakistriphenylphosphine Palladium (0.9g, 0.7mmol) was dissolved in 100ml of dry 1,4-dioxane solution, heated and refluxed for 4 hours. After the reaction was completed, 1N dilute hydrochloric acid was added to quench the reaction, extracted with ethyl acetate, and washed with saturated brine. , dried over anhydrous sodium sulfate, concentrated and purified with a silica gel column to obtain compound 2-methylpyridine-4-carbonitrile (2.5g, 57.6%). MSm/z[ESI]: 119.1[M+1].

Applications of 2-methylpyridine-4-carbonitrile

2-Methylpyridine-4-carbonitrile can be used as a pharmaceutical synthesis intermediate. If the following reaction occurs:

Step 1) Preparation of compound 1-3: Combine compound 2-methylpyridine-4-carbonitrile (2.5g, 20.8mmol), triethylamine (8.6ml, 62.4mmol), and hydroxylamine hydrochloride (2.9g, 41.6 mmol) was dissolved in 50 ml of 95% ethanol, and stirred under reflux conditions for 2 hours. After the reaction, the ethanol was concentrated, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and purified with a silica gel column to obtain the compound. 1-3 (2.9g, 93.4%). MSm/z[ESI]: 152.1[M+1].

Step 2: Preparation of compound 1-4: Compound 1-3 (2.9g, 19.4mmol), BOC-glycine (deuterated tetrahydrofuran 3.4g, 19.4mmol), N,N-diisopropyl ethyl Amine (10.1ml, 58.2mmol), 2-(7-azobenzotriazole)-N,N,N’,N’-tetramethylurea hexafluorophosphate (8.8g, 23.3mmol) were dissolved in Add 100 ml of dry N,N-dimethylformamide, raise the temperature to 100°C and stir overnight. After the reaction is completed, add 150 ml of ice water to the system to quench the reaction, extract with ethyl acetate, wash with saturated brine, and dry over anhydrous sodium sulfate. After concentration, it was purified with a silica gel column to obtain compound 1-4 (2.9 g, 52.1%). MSm/z[ESI]: 291.1[M+1].