Sodium Hydroxide → HCID 136413214, compound

2-Nitro-4-[2-(5-propyl-[1,2,4]oxadiazol-3-yl)-vinyl]-phenol (compound of Example 11; 0.2 g, 0.72 mmol) was dissolved in ethyl acetate (5 mL) to which stannous chloride was added and the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was cooled to 0° C. followed by addition of aqueous sodium hydroxide solution to adjust pH to 10. The reaction mixture was extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with water (2×10 mL) and brine (10 mL). The organic phase obtained was dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by column chromatography (silica gel, 0.5 methanol in chloroform) to afford the title compound.

1. additionwas added
2. temperatureThe reaction mixture was cooled to 0° C.
3. extractionThe reaction mixture was extracted with ethyl acetate (2×5 mL)
4. washThe combined organic layers were washed with water (2×10 mL) and brine (10 mL)
5. customThe organic phase obtained
6. dry with materialwas dried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customto obtain a crude product, which
9. customwas purified by column chromatography (silica gel, 0.5 methanol in chloroform)

ORD record

ord-83aafeeecf8b40369eaafa26e2018fe1

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629277B2