Stannous Chloride → HCID 10012917, compound

Participants

Reaction Steps

To a solution of diethyl-(2-fluoro-5-nitro-benzyl)-amine (0.155 mg, 0.69 mmoles) in THF (20 mL) was added a solution of SnCl2 (520 mg, 2.74 mmoles) in THF (5 mL) and HCl 1M (2.1 mL). The reaction mixture was refluxed for 8 h and concentrated. Saturated solution of NaHCO3 was added until pH8. Aqueous layer was extracted with CH2Cl2 (5×50 mL). The organic layer was dried over MgSO4, filtered, evaporated. Expected compound was precipited with MeOH and purified by TLC DCM/MeOH/NH4OH//9/1/0.2) and obtained as a yellow oil (98 mg, 73% yield). MALDI-TOF: m/z 197.2 [M+H]+. 1H NMR (300 MHz, CDCl3) δ6.80; (dd, J=8.7 Hz and 8.7 Hz, 1H), 6.75; (dd, J=5.7 Hz and 3.0, 1H), 6.49; (ddd, J=8.7 Hz, 3.9 Hz and 3.0 Hz, 1H), 3.65-3.75; (s large, 2H), 3.57; (s, 2H), 2.57; (q, J=7.2 Hz, 4H), 1.07; (t, J=7.2 Hz, 6H). 13C NMR (75 MHz, CDCl3) δ118.2; (CH, d, J=3.8 Hz), 116.4; (CH, d, J=23.3 Hz), 115.7; (CH, d, J=7.9 Hz), 49.8; (CH2), 47.3; (CH2), 12.4; (CH3).

Provenance & Evidence