Sodium Hydroxide → HCID 90203662, compound

Temperature

80 °C

Powdered NaOH (3 g, 75 mmol) was added to a suspension of 5-bromo-2-methyl-4-nitropyridine 1-oxide (11.7 g, 50 mmol; CAN 62516-08-9) in cyclopropylmethanol (89 g, 100 mL, 1.23 mol). The mixture was stirred for 4 h at 80° C. After evaporation to dryness ethyl acetate (400 mL) and water (400 mL) were added. The layers were separated and the aqueous phase was extracted four more times with ethyl acetate (250 mL). The combined extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated to a volume of 100 mL and heptane (100 mL) was added dropwise under stirring. The precipitate was collected washed with ethyl acetate/heptane 1/2 (3×20 mL) and dried in vacuo to give the title compound (10.4 g, 80%) as light brown solid; LC-MS (UV peak area, m/z) 100%, 258.0125 (MH+).

1. customAfter evaporation to dryness ethyl acetate (400 mL) and water (400 mL)
2. additionwere added
3. customThe layers were separated
4. extractionthe aqueous phase was extracted four more times with ethyl acetate (250 mL)
5. washThe combined extracts were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationThe filtrate was concentrated to a volume of 100 mL and heptane (100 mL)
9. additionwas added dropwise
10. stirringunder stirring
11. customThe precipitate was collected
12. washwashed with ethyl acetate/heptane 1/2 (3×20 mL)
13. customdried in vacuo

ORD record

ord-1151cdd4600b4eab85f4122b0d99e6a5

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409866B2