Nitric Acid → HCID 23238949, compound

2,3-Xylenol (5 g, 40.9 mmol) was dissolved in toluene (100 ml), and the solution was added with 2-aminopyridine (0.3 g, 3.2 mmol). The mixture was added with thionyl chloride (3.3 ml) at room temperature with stirring, and then stirred at 7 C.° for 15 hours. The reaction mixture was cooled to room temperature, and then excessive reagents and solvent were evaporated under reduced pressure to obtain an oily substance. The substance was dissolved in acetic acid (12.5 ml), and the solution was added with concentrated sulfuric acid (50 ml), and then added dropwise with a mixed acid (2.5 ml of 70% nitric acid+10 ml of concentrated sulfuric acid) at room temperature over 30 minutes or more. The mixture was further stirred for 2 hours, and poured into iced water (500 ml). The precipitates were collected by filtration, and dried to obtain a crude product (3.8 g). The product was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 v/v) to obtain the title compound (1.5 g).

1. stirringstirred at 7 C.° for 15 hours
2. customexcessive reagents and solvent were evaporated under reduced pressure
3. customto obtain an oily substance
4. stirringThe mixture was further stirred for 2 hours
5. filtrationThe precipitates were collected by filtration
6. customdried
7. customto obtain a crude product (3.8 g)
8. customThe product was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 v/v)

ORD record

ord-0d3931a083ba445e9a3b7d7e224d8292

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07045516B1