Hydrazine hydrate (1:1) → (5-Bromopyridin-2-yl)methanamine
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[N:6][CH:7]=1.O.NN>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 2-((5-bromopyridin-2-yl)methyl)isoindoline-1,3-dione from Step 1 of Example 265 (630 mg, 1.987 mmol) and hydrazine monohydrate (0.484 mL, 9.93 mmol) was heated to 70° C. for 1.5 hr. A thick suspension formed. after cooling to rt, the reaction mixture was diluted with 20 ml of EtOH, filtered and the filter cake was washed with EtOH. The filtrate was concentrated to ⅓ volume and was refiltered. Concentration of that filtrate afforded (5-bromopyridin-2-yl)methanamine (364 mg, 1.946 mmol, 98% yield) as a colorless semisolid. 1H NMR (400 MHz, DMSO-d6) δ 8.58 (d, J=2.2 Hz, 1H), 7.99 (dd, J=8.4, 2.4 Hz, 1H), 7.45 (dd, J=8.4, 0.4 Hz, 1H), 3.77 (s, 2H). MS (ES+) m/z: 187.12, 189.07 (M+H); LC retention time: 0.298 min (analytical HPLC Method O).