Morpholine → HCID 178526366, compound

A mixture of 2-chloro-5-nitropyridine (2 g, 12.6 mmol) and morpholine (4.4 g, 50.5 mmol) was stirred at a room temperature for 1 hour. Water was added to the reaction mixture and the crystals separated out therefrom were filtered to obtain yellow powdery crystals. Methanol (30 ml) and palladium carbon (0.25 g) were added thereto, the mixture was stirred in a hydrogen atmosphere at a room temperature for 4 hours, insoluble matters were filtered off using Celite and the filtrate was concentrated under a reduced pressure. To the resulting residue were added methanol (20 ml) and dimethylformamide dimethylacetal (1.81 g, 15.2 mmol), followed by stirring under refluxing for 2 hours. The reaction mixture was cooled down to room temperature and concentrated under a reduced pressure, and methanol (20 ml) and hydroxylamine hydrochloride (1.05 g, 15.2 mol) were added thereto, followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated under a reduced pressure and a saturated aqueous solution of sodium hydrogen carbonate (10 ml) was added thereto, followed by extracting with ethyl acetate. The organic layer was dried over MgSO4, concentrated under a reduced pressure, purified by an NH type silica gel column chromatography (developing solvents; n-hexane:ethyl acetate=1:1) and recrystallized from ethyl acetate to obtain the title compound (0.985 g) (the compound 127 in Table 1 which will be shown after) in colorless powder.

1. customthe crystals separated out
2. filtrationtherefrom were filtered
3. customto obtain yellow powdery crystals
4. filtrationinsoluble matters were filtered off
5. concentrationthe filtrate was concentrated under a reduced pressure
6. stirringby stirring
7. temperatureunder refluxing for 2 hours
8. temperatureThe reaction mixture was cooled down to room temperature
9. additionwere added
10. stirringby stirring at room temperature for 4 hours
11. concentrationThe reaction mixture was concentrated under a reduced pressure
12. additiona saturated aqueous solution of sodium hydrogen carbonate (10 ml) was added
13. extractionby extracting with ethyl acetate
14. dry with materialThe organic layer was dried over MgSO4
15. concentrationconcentrated under a reduced pressure
16. custompurified by an NH type silica gel column chromatography (developing solvents; n-hexane:ethyl acetate=1:1)
17. customrecrystallized from ethyl acetate

ORD record

ord-d98fa77f80ac412d9478257349ab6374

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07214714B2