Some common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, molecular formula is C12H10ClNO, 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. Quality Control of 2-(4-Chlorophenoxy)aniline
A stirred solution of Boc-glycine (1.50 mmol), PyBOP (1.60 mmol) and DIPEA (3.50 mmol) in dichloromethane (10 mL) was cooled to 0 C with an ice bath. To this solution 2-(4-chlorophenoxy)aniline (1.50 mmol), dissolved in a minimum amount of dichloromethane, was added dropwise. The reaction mixture was allowed to warm to room temperature and was then stirred for 24 h. Thereafter, an aqueous work-up was performed similar to that of compounds 1-8. The resulting oil was further purified by column chromatography over silica gel(dichloromethane/methanol 200:1) to give a slightly orange solid (358 mg, 0.95 mmol, 63%); m.p.: 50-51 C; IR (KBr): [cm-1] nu = 3409 (m, N-H), 3342 (s, N-H), 1691 (br, s, C=O); 1H-NMR: (600 MHz, DMSO-d6): delta [ppm] = 1.34 (s, 9H, CH3), 3.71 (d, J = 6.1 Hz, 2H, CH2), 6.87-7.06 (m, 3H, arom. H), 7.05-7.30 (m, 3H, arom. H), 7.35-7.53 (m, 2H, arom. H), 8.12 (d, J = 7.7 Hz, 1H, NH), 9.33 (s, 1H, NH); 13C-NMR (151 MHz, DMSO-d6) delta [ppm] = 28.00 (3C, CH3), 43.92 (CH2), 118.82, 119.90 (2C), 122.35, 124.15, 124.63, 129.70 (2C) (CH), 78.17, 127.17, 129.64, 146.09, 155.47, 155.86, 168.51 (C); EI-MS: m/z (%): 376.1 [M]+ (11), 219.1 [M – 157]+ (100); HREI-MS: calcd. for C19H21ClN2O4 376.11844, found 376.11803; HPLC: 96.3% at 254 nm, 96.3% at 280 nm; tR = 4.84 min, tM(DMSO) = 1.06 min(ACN/H2O = 60:40), lambdamax [nm] = 230; HPLC-gradient: 95.8%, tR = 12.80 min, tM(DMSO) = 1.28 min.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2770-11-8, its application will become more common.
Reference:
Article; Weidner, Thomas; Nasereddin, Abed; Preu, Lutz; Gruenefeld, Johann; Dzikowski, Ron; Kunick, Conrad; Molecules; vol. 21; 2; (2016);,
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