HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 5-Methylpicolinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 2-Bromo-5-methylpyridine | HCID 564216 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-Methylpicolinonitrile | HCID 74183 | 56% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07112595B2 |
| Source dataset | uspto-grants-2006_09 |
| ORD ID | ord-fec0df1fa3854b5aafa7091e0aa6fee8 |
| Source note | uspto-grants-2006_09 |