Sodium Hydroxide → 8-((5-Methyl-1H-imidazol-4-yl)methyl)quinoline

Temperature

160 °C

A mixture of (4) (0.71 g, 1.48 mmol) and red phosphorus (0.46 g, 14.18 mmol) in hydroiodic acid (57% in water, 6 mL) was heated in a sealed tube at 160° C. overnight. The reaction mixture was cooled to room temperature, and the sealed tube was slowly opened to release the gas built up inside. The content was poured into crushed ice, and carefully basified with NaOH (aq) to pH>7. The aqueous layer was diluted with chloroform/isopropanol (3:1, 100 mL). The mixture was filtered through a bed of Celite to removed phosphorus. The layers were separated and the aqueous layer was extracted twice with chloroform/isopropanol (3:1, 100 mL). The pooled to organic layers were dried over magnesium sulfate. The mixture was filtered and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 2% ammonia saturated methanol in dichloromethane to give 8-((5-methyl-1H-imidazol-4-yl)methyl)quinoline (5) as a light yellow solid (0.23 g, 1.05 mmol, 71% yield). 30 mg of (5) was passed through reverse phase HPLC to give 26.5 mg of an analytically pure sample.

1. temperatureThe reaction mixture was cooled to room temperature
2. additionThe content was poured
3. custominto crushed ice
4. filtrationThe mixture was filtered through a bed of Celite
5. customto removed phosphorus
6. customThe layers were separated
7. extractionthe aqueous layer was extracted twice with chloroform/isopropanol (3:1, 100 mL)
8. dry with materialwere dried over magnesium sulfate
9. filtrationThe mixture was filtered
10. customthe solvents were removed under vacuum
11. customThe residue was purified by chromatography on silica gel with 2% ammonia saturated methanol in dichloromethane

ORD record

ord-b5f826b6b0cb4ed2a4864e60db892a10

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119807B2