Hydrazine hydrate (1:1) → 1-(3-Phenylbenzo[b]thiophen-2-yl)ethanamine
Reaction equation
[C:1]1([C:7]2[C:8]3[CH:28]=[CH:27][CH:26]=[CH:25][C:9]=3[S:10][C:11]=2[CH:12]([N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>CCO>[C:1]1([C:7]2[C:8]3[CH:28]=[CH:27][CH:26]=[CH:25][C:9]=3[S:10][C:11]=2[CH:12]([NH2:14])[CH3:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 2-(1-(3-phenylbenzo[b]thiophen-2-yl)ethyl)isoindoline-1,3-dione (170 mg, 0.443 mmol) and hydrazine, monohydrate (0.215 mL, 4.43 mmol) in EtOH (5 mL) was heated to 50° C. overnight. After 18 h, a precipitate had developed. The precipitate was removed by filtration, rinsed with EtOH, and concentrated under reduced pressure. The concentrate was dissolved in DCM, adsorbed onto silica gel and purified by column chromatography using 10% of MeOH in DCM as eluent to give 1-(3-phenylbenzo[b]thiophen-2-yl)ethanamine as a colorless, crystalline solid: 1H NMR (400 MHz, CDCl3) δ 1.51 (d, J=6.5 Hz, 3H), 1.74 (br. s., 2H), 4.55 (q, J=6.5 Hz, 1H), 7.30-7.38 (m, 2H), 7.41-7.57 (m, 6H), 7.87-7.91 (m, 1H); LC-MS (ESI)] m/z 237.1 [M-16]−.