Reference of 2770-11-8, These common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A solution of the aniline (250 mg, 1.14 mmol), l-acetyl-3-indolecarboxaldehyde (107 mg, 0.57 mmol), NaBH(OAc)3 (302 mg, 1.43 mmol) and AcOH (205 mg, 3.42 mmol) in 1,2-DCE (3 ml) was stirred at room temperature for 16 h. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate (5 ml) and extracted with EtOAc (3 x 5 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo before purification by flash chromatography (eluant; 8:2 hexane:EtOAc to EtOAc) proceeded to afford the desired product which was recrystallised from EtOAc and hexane to afford a cream solid (174.1 mg, 78%).1H NMR: (CDCl3, 270 MHz): delta 2.56 (3H, s, CH3), 3.77 (IH, br s, NH), 4.47 (2H, br s,CH2), 6.65-7.50 (12H, m, ArH), 8.41 ppm (IH, d, J= 7.9 Hz, ArH). 13C NMR: (CDCl3, 67.93 MHz): 5 24.1, 39.7, 112.1, 117.0, 117.6, 118.5, 119.0, 119.6,120.1, 123.0, 123.7, 125.5, 125.7, 128.0, 129.7, 136.1, 140.0, 143.5, 156.2, 168.6 ppm.LCMS: 1.550 min, (95% MeOH : 5% water at 1.0 ml/min), AP”: 389.20.HPLC: 3.410 min, 95.90% purity, (isocratic, 90% acetonitrile : 10% water at 1.0 ml/min).HRMS (MicroTOF): C23H20ClN2O2 requires 391.1208, found 391.1194. M.Pt. 107-1080C.
Statistics shows that 2-(4-Chlorophenoxy)aniline is playing an increasingly important role. we look forward to future research findings about 2770-11-8.
Reference:
Patent; STERIX LIMITED; WO2009/66072; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics