Acetic Acid → (6-Methylpyridin-2-yl)methanamine

To (E)-6-methylpicolinaldehyde oxime (0.635 g, 4.66 mmol)/acetic acid (267 μL, 4.66 mmol)/ethanol (10 mL) solution was added portionwise zinc dust (5.19 g, 79 mmol) over 30 min. The resulting mixture was stirred for additional 30 min. LCMS of reaction aliquot indicated reaction was completed. The zinc precipitates in reaction mixture was removed by filtration, and the filtrate was concentrated. The residue was basified to pH>12 with excess sat. KOH (˜7 mL), and stirred with Et2O (30 mL). The Et2O layer was collected, dried over Na2SO4, and concentrated. The residue was redissolved in EtOAc(15 mL), dried over Na2SO4, and concentrated. (6-Methylpyridin-2-yl)methanamine was obtained as a colorless oil (385 mg, 3.15 mmol, 67.6%). LCMS (m/z) 123.2 (MH+) 0.15 min.

1. customLCMS of reaction aliquot indicated reaction
2. customThe zinc precipitates in reaction mixture
3. customwas removed by filtration
4. concentrationthe filtrate was concentrated
5. stirringstirred with Et2O (30 mL)
6. customThe Et2O layer was collected
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. dissolutionThe residue was redissolved in EtOAc(15 mL)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated

ORD record

ord-ff5918e3df0d434fb1571b7256986869

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242996B2