HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuric Acid → Ethyl 2-picolinoylnicotinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Furo[3,4-b]pyridine-5,7-dione | HCID 69688 | — |
| Reactant | Lupinisoflavone B | HCID 632835 | — |
| Reactant | 1,3,8-trihydroxy-2-[(E)-4-hydroxy-3-methylbut-2-enyl]-[1]benzofuro[2,3-b]chromen-11-one | HCID 101613214 | — |
| Reactant | HCID 178506720 | HCID 178506720 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | 2,3-Diethyl 2,3-pyridinedicarboxylate | HCID 10889517 | — |
| Product | Ethyl 2-picolinoylnicotinate | HCID 117925977 | — |
| Product | Ethyl 3-picolinoylpicolinate | HCID 117926477 | — |
Reaction Steps
Each of the Rilyazines RL-1 through RL-4 may be synthesized according to the procedure of Scheme 1. Furo[3,4-b]pyridine-5,7-dione is reacted with ethanol in the presence of an acid, such as H2SO4, resulting in diethyl pyridine-2,3-dicarboxylate (1), which is then reacted with freshly-prepared pyridin-2-yl lithium to afford ethyl 2-picolinoylnicotinate (2) and ethyl 3-picolinoylpicolinate (3). Separation of the isomers (2) and (3) by chromatography and their reactions with cyclohexylhdrazine hydrochloride affords the ketone-Rilyazines RL-1 and RL-3, which may then be converted to the corresponding thione-Rilyazines RL-2 and RL-4 by reaction with Lawesson reagent.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09394299B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-bab5a582bc5c42f8a02b9386e882ad15 |
| Source note | uspto-grants-2016_07 |