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Dimethylformamide → 5-Methylpicolinonitrile
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Dichloromethane | HCID 6344 | — |
| 反応物 | 2-Bromo-5-methylpyridine | HCID 564216 | — |
| 触媒 | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| 触媒 | Zinc | HCID 23994 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 5-Methylpicolinonitrile | HCID 74183 | 56% |
反応手順
A mixture of 2-bromo-5-methylpyridine (2.001 g, 11.63 mmol), zinc cyanide (830 mg, 7 mmol), zinc (dust, 35 mg, 0.53 mmol), [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II), complex with dichloromethane (1:1) (192.5 mg, 0.24 mmol) in N,N-dimethylformamide (10 mL) was heated at reflux for 16 hours. After cooling, the reaction was diluted with ethyl acetate and extracted with water and brine. The organic solution was filtered through a plug of silica gel, washing dichloromethane. Removal of the solvent in vacuo, afforded 770 mg (56%) of 5-methyl-2-cyano-pyridine.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06660753B2 |
| 出典データセット | uspto-grants-2003_12 |
| ORD ID | ord-2e27af0b4bbc4ccf8085e124a9ccd2b1 |
| 出典メモ | uspto-grants-2003_12 |