Hydrazine → (4-Bromo-2-ethylphenyl)methanamine
Reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2C(=O)C3C(=CC=CC=3)C2=O)=[C:4]([CH2:20][CH3:21])[CH:3]=1.NN>C(Cl)(Cl)Cl.C(O)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH2:7])=[C:4]([CH2:20][CH3:21])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(4-Bromo-2-ethyl-benzyl)-isoindole-1,3-dione (4 g, 11.7 mmol) and hydrazine (1.8 mL, 58.3 mmol) in chloroform:ethanol (1:1.5, 250 mL) were refluxed for 4 h. The mixture was cooled to room temperature and filtered through a pad of celite. The solution was diluted in water and partitioned. The organic layer was washed with water, saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and then concentrated in vacuo to a yellow oil (2.2 g, 88%). 1H NMR (300 MHz, CDCl3): δ ppm 1.23 (t, J=7.54 Hz, 3 H) 1.65 (s, 2 H) 2.66 (q, J=7.60 Hz, 2 H) 3.84 (s, 2 H) 7.19–7.23 (m, 1 H) 7.30–7.34 (m, 2 H).