HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 5-{[(Propan-2-yl)oxy]methyl}pyridine-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 2-Chloro-5-{[(propan-2-yl)oxy]methyl}pyridine | HCID 21897801 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Solvent | Water methylene chloride | HCID 21908982 | — |
| Product | 5-{[(Propan-2-yl)oxy]methyl}pyridine-2-carbonitrile | HCID 21897415 | — |
Reaction Conditions
| Temperature | 180 °C |
|---|
Reaction Steps
In a microwave reaction tube was placed 2-chloro-5-isopropoxymethyl-pyridine (0.12 g, 0.66 mmol), Zn(CN)2 (0.077 g, 0.66 mmol), tetrakis(triphenylphosphino)dipalladium (76 mg, 0.066 mmol), DMF (2 mL). The reaction mixture was heated at 180° C. for 5 minutes. The resulted mixture was worked up by CH2Cl2/H2O. The CH2Cl2 layer was dried and concentrated to give the crude product. The crude was purified by column chromatography by using 30% EtOAc/Hexane. 1H NMR (CDCl3, 400 MHz) δ 1.26 (d, 6H), 3.73 (m, 1H), 4.59 (s, 2H), 7.68 (d, 1H), 7.85 (m, 1H), 8.67 (s, 1H). Exact mass calculated for C10H12N2O 176.09, found 177.2 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08410119B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-42854645e59f4994a7fff712a0820b1a |
| Source note | uspto-grants-2013_04 |