HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 643282Generated: October 28, 2026
Sodium Cyanide → 6-(Hydroxymethyl)pyridine-3-carbonitrile
https://huagongshe.com/reaction/643282
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | (5-Bromopyridin-2-yl)methanol | HCID 5200169 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Propionitrile | HCID 7854 | — |
| Product | 6-(Hydroxymethyl)pyridine-3-carbonitrile | HCID 53427687 | 48% |
Reaction Steps
(5-Bromo-pyridin-2-yl)-methanol (1.0 g), NaCN (521 mg), Pd(PPh3)4 (612 mg), and CuI (200 mg) were taken up in degassed EtCN and heated at 110° C. (4 h). The solution was partitioned between EtOAc and 10% NH4OH(aq.). The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave a yellow solid. Purification via flash chromatography (1/2 hexanes/EtOAc, SiO2) gave 341 mg (48%) of (5-cyano-pyridin-2-yl)-methanol as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07700597B2 |
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| Source dataset | uspto-grants-2010_04 |
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| ORD ID | ord-5a42732d066640369b4b23029fea2976 |
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| Source note | uspto-grants-2010_04 |
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