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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 719474Generated: October 30, 2026

Dimethylformamide → 5-{[(Propan-2-yl)oxy]methyl}pyridine-2-carbonitrile

https://huagongshe.com/reaction/719474

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant2-Chloro-5-{[(propan-2-yl)oxy]methyl}pyridineHCID 21897801—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
SolventWater methylene chlorideHCID 21908982—
Product5-{[(Propan-2-yl)oxy]methyl}pyridine-2-carbonitrileHCID 21897415—

Reaction Conditions

Temperature180 °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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07132426B2
Source datasetuspto-grants-2006_11
ORD IDord-7ea0b5e8cec84737a68142f7532603e0
Source noteuspto-grants-2006_11