2-Amino-3-Hydroxypyridine → HCID 70248964, compound

A mixture of 2-amino-3-hydroxypyridine (2.18 g, 19.4 mmol), bromo-1,1,1-trifluoroacetone (9.1 g, 42.6 mmol), and molecular sieves (6.3 g, 8–12 mesh beads) in anhydrous methanol (50 mL) was refluxed for 24 h. After the molecular sieves were filtered off and the solvent was evaporated in vacuo, the residue was dissolved in water (150 mL) and the resultant mixture was extracted with diethyl ether (2×150 mL). The combined organic extracts were dried over anhydrous sodium sulphate and the solvent was evaporated in vacuo to provide the crude 8-hydroxy-2-(trifluoromethyl)imidazo[1,2-α]pyridine. Purification by column chromatography using as eluent a mixture of ethyl acetate and isopropylamine (98:2 v/v) yielded 0.7 g of pure 8-hydroxy-2-(trifluoromethyl)imidazo[1,2-α]pyridine.

1. temperaturewas refluxed for 24 h
2. filtrationAfter the molecular sieves were filtered off
3. customthe solvent was evaporated in vacuo
4. dissolutionthe residue was dissolved in water (150 mL)
5. extractionthe resultant mixture was extracted with diethyl ether (2×150 mL)
6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
7. customthe solvent was evaporated in vacuo
8. customto provide the crude 8-hydroxy-2-(trifluoromethyl)imidazo[1,2-α]pyridine
9. customPurification by column chromatography
10. additiona mixture of ethyl acetate and isopropylamine (98:2 v/v)

ORD record

ord-5d775eefd6114ab89b24dc3793e789d3

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105534B2