Iodoethane → HCID 19067740, compound

Temperature

90 °C

A mixture of ethyl 6-chloro-4-hydroxynicotinate (3.7 g), powdered potassium carbonate (3.7 g), iodoethane (5 ml) and dimethylformamide (50 ml) is well stirred for 7 hours at 90° C. After cooling, the reaction mixture is filtered and the solvent evaporated off. The residue is treated with icy water (30 ml) and extracted with dichloromethane (2×30 ml). The combined extract are dried and evaporated to dryness. The residue is boiled 90 minutes with 1N sodium hydroxide (18 ml). After cooling the solution is extracted with diethyl ether (30 ml), that is discharged. The alkaline solution is concentrated to small volume, cooled and acidified to pH 4 with 1N hydrochloric acid. The white material that precipitates is collected and crystallized from ethanol to give 6-chloro-1,4-dihydro-1-ethyl-4-oxo-3-pyridine-carboxylic acid (3 g) m.p. 155°-57° C.

1. temperatureAfter cooling
2. filtrationthe reaction mixture is filtered
3. customthe solvent evaporated off
4. additionThe residue is treated with icy water (30 ml)
5. extractionextracted with dichloromethane (2×30 ml)
6. extractionThe combined extract
7. customare dried
8. customevaporated to dryness
9. waitThe residue is boiled 90 minutes with 1N sodium hydroxide (18 ml)
10. temperatureAfter cooling the solution
11. extractionis extracted with diethyl ether (30 ml), that
12. concentrationThe alkaline solution is concentrated to small volume
13. temperaturecooled
14. customThe white material that precipitates
15. customis collected
16. customcrystallized from ethanol

ORD record

ord-0811c44a62684144bf53e07dd039c20a

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05786350