Hydrazine hydrate (1:1) → 3-(Aminomethyl)-5-bromopyridine

A solution of 2-((5-bromopyridin-3-yl)methyl)isoindoline-1,3-dione (LIII) (1.9 g, 6.0 mmol, 1 eq) and hydrazine hydrate (2.0 g, 40 mmol, 6 eq) in EtOH (20 mL) was heated at 70° C. for 3 h. The mixture was filtered through a Celite® pad and the filtrate was concentrated in vacuo, the crude product was dissolved in 1N HCl solution (15 mL) and concentrated to dryness, then it was washed with acetone (10 mL x 3), the precipitate was collected by filtration, dried in vacuo to give (5-bromopyridin-3-yl)methanamine (LIV) (1.3 g, 6.95 mmol, 97.7% yield) as a white solid. 1H NMR (D2O, 500 MHz) δ ppm 4.34 (s, 2H), 8.56 (s, 1H), 8.75 (d, J=1.2 Hz, 1H), 8.91 (d, J=1.6 Hz, 1H). ESIMS found for C6H7BrN2 m/z 187 (M+H).

1. filtrationThe mixture was filtered through a Celite® pad
2. concentrationthe filtrate was concentrated in vacuo
3. dissolutionthe crude product was dissolved in 1N HCl solution (15 mL)
4. concentrationconcentrated to dryness
5. washit was washed with acetone (10 mL x 3)
6. filtrationthe precipitate was collected by filtration
7. customdried in vacuo

ORD record

ord-5d0027d992e74262b994aadef81a83d0

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199991B2