HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2196370Generated: November 2, 2026
Dimethylformamide → 3-Chloro-5-hydroxypicolinonitrile
https://huagongshe.com/reaction/2196370
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 5,6-Dichloropyridin-3-yl acetate | HCID 14595222 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | argon Zn | HCID 85978949 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | 3-Chloro-5-hydroxypicolinonitrile | HCID 66665473 | — |
Reaction Steps
To a solution of acetic acid 5,6-dichloro-pyridin-3-yl ester (CA 110861-18-2, Synthesis, 1990, 499) (4.88 g, 23.6 mmol) in anhydrous DMF (45 ml) was added after degasing with argon Zn-dust (70 mg, 1.07 mmol), Zn(CN)2 (1.28 g, 10.9 mmol) and DPPF PdCl2 (966 mg, 1.18 mmol) and the reaction mixture was heated for 6 h at 130° C. and 18 h at 150° C. The reaction mixture was diluted with TBME and H2O, filtered over Celite, and the product was extracted with TBME. Combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated. The title compound was obtained as a beige solid after crystallization from EtOAc-hexane: TLC (CH2Cl2-MeOH 19:1): Rf=0.22;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08338413B1 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-f80c641d489e466ca62a113548426d70 |
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| Source note | uspto-grants-2012_12 |
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