O-Methylhydroxylamine hydrochloride → HCID 86692184, compound

To a stirring solution of 2-bromo-1-(5-ethylpyridin-2-yl)ethanone hydrobromide (1.024 g, 3.314 mmol; Supplier=Kalexsyn; Lot=1003-TTP-185) in EtOH (10 ml) was added methoxylamine hydrochloride (553.5 mg, 6.628 mmol). Left to stir at RT overnight. The reaction mixture was evaporated in vacuo. The residue was dissolved in DCM and an equal volume of saturated NaHCO3 was added and the biphasic mixture stirred for 30 minutes. The phases were separated and the aqueous phase was extracted with DCM. The combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo to afford a pale yellow oil which crystallized upon standing. 1H-NMR (CDCl3): δ 8.50 (s, 1H), 7.87 (d, J=8.3 Hz, 1H), 7.59 (m, 1H), 4.79 (s, 1H), 4.64 (s, 1H), 4.13 (d, J=4.4 Hz, 3H), 2.70 (q, J=7.7 Hz, 2H), 1.28 (t, J=7.7 Hz, 3H). HPLC: 3.429 min., 30 area % and 3.621 min., 31 area % @ 210 nm; 3.414 min., 36 area % and 3.618 min., 36 area % @ 210 nm. MS (ESI—) for C10H13BrN2O m/z 258.2 (M+H)+.

1. waitLeft
2. customThe reaction mixture was evaporated in vacuo
3. dissolutionThe residue was dissolved in DCM
4. additionan equal volume of saturated NaHCO3 was added
5. stirringthe biphasic mixture stirred for 30 minutes
6. customThe phases were separated
7. extractionthe aqueous phase was extracted with DCM
8. dry with materialThe combined organic phases were dried (Na2SO4)
9. filtrationfiltered
10. customevaporated in vacuo
11. customto afford a pale yellow oil which
12. customcrystallized
13. custom3.429 min., 30 area
14. custom3.621 min., 31 area
15. custom3.414 min., 36 area
16. custom3.618 min., 36 area

ORD record

ord-5b8a29bb05ac4489aa7c66cedfb83828

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895748B2