Ethyl bromoacetate → HCID 18317825, compound

The mixture of 6-iodo-2-picolin-5-ol (235 mg, 1.0 mmol), potassium carbonate (455 mg, 3.3 mmol), ethyl bromoacetate (250 mg, 1.49 mmol) and acetone (15 ml) was refluxed for 15 h. After cooling, the mixture was filtered to remove potassium carbonate. The filtrate was concentrated under reduced pressure. To this residue, 10 ml dioxane and 14 ml 5% sodium hydroxide solution were added. After the mixture was stirred at room temperature overnight, it was acidified with concentrated hydrochloric acid to pH 3, and then extracted three times with ethyl acetate (20 ml each). Organic phases were combined, washed with water and brine, dried over magnesium sulfate, filtered, and then evaporated in vacuo. The residue was recrystallized from ethanol and petroleum ether to give 165 mg 6-iodo-2-methylpyridine-5-oxyacetic acid as white crystals, mp 170-172° C.

1. temperaturewas refluxed for 15 h
2. temperatureAfter cooling
3. filtrationthe mixture was filtered
4. customto remove potassium carbonate
5. concentrationThe filtrate was concentrated under reduced pressure
6. additionTo this residue, 10 ml dioxane and 14 ml 5% sodium hydroxide solution were added
7. extractionextracted three times with ethyl acetate (20 ml each)
8. washwashed with water and brine
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. customevaporated in vacuo
12. customThe residue was recrystallized from ethanol and petroleum ether

ORD record

ord-73ef7ffe7fa4445888dcaced88d53c24

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE039707E1