Methylhydrazine → 3,5-Dibromo-4-[(2-methylhydrazinylidene)methyl]pyridine
Reaction equation
[CH3:1][NH:2][NH2:3].[Br:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Br:13])[C:10]=1[CH:11]=O>CC(O)C>[Br:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Br:13])[C:10]=1[CH:11]=[N:3][NH:2][CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methylhydrazine (1.06 mL, 19.3 mmol) was added to a solution of 3,5-dibromopyridine-4-carbaldehyde (3.4 g, 13 mmol) in 2-propanol (20 mL). After 3 hours at room temperature, the reaction mixture was concentrated in vacuo, dissolved in ethyl acetate, and washed with saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the product as a solid. Yield: 3.20 g, 10.9 mmol, 84%. 1H NMR (400 MHz, DMSO-d6) δ 8.62 (s, 2H), 7.24-7.26 (m, 1H), 2.89-2.91 (m, 3H).