A facile C-N bond formation: One-pot reaction of phenols and amines via smiles rearrangement

Synlett

Volumn , Issue 3, 2010, Pages 483-487

  Yang, Hao ^a   Li, Zhu Bo ^a   Shin, Dong Soo ^b   Wang, Li Ying ^a   Zhou, Jia Zhou ^a   Qiao, Hong Bo ^a   Tian, Xiao ^a   Ma, Xiao Yan ^a   Zuo, Hua ^a  

^a SOUTHWEST UNIVERSITY   (China)

^b Changwon National University   (South Korea)

Author keywords

Amine; C N coupling; One pot; Smiles rearrangement; Synthesis

Indexed keywords

AMINE; CARBON; NITROGEN; PHENOL DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; REACTION ANALYSIS;

EID: 76249087140     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219190     Document Type: Article

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35. General Procedure of One-Pot Reaction for the CN Bond Formation (8) To a magnetically stirred solution of the appropriate primary amine 7 (1.0 mmol) and Cs2CO3 (3.2 mmol) in dry DMF cooled by ice bath were added chloroacetyl chloride (1.2 mmol) and 6 (1.1 mmol). The reaction mixture was then stirred for 30 min at r.t. and placed into microwave oven (600 W, 120 C) and irradiated for 2060 min or under conventional heating for 36 h. The solvent was removed under vacuum and H2O (20 mL) was added into the residue. It was then extracted by EtOAc. The combined organic layers were dried over anhyd MgSO4 and evaporated under vacuum to obtain the crude product. Pure product was obtained by column chromatography on silica gel.
36. 2-Chloro-N-(4-methoxyphenyl)-5-methylaniline (8l) Orange oil. IR (KBr): n = 3402, 3038, 2999, 2952, 2930, 2850, 2834, 1600, 1580, 1513, 1455, 1441, 1398, 1294, 1245, 1180, 1044, 829, 794 cm1. 1H NMR (300 MHz, CDCl3): d = 2.20 (s, 3 H, CH3), 3.81 (s, 3H, OCH3), 5.88 (br s , 1 H, NH), 6.53 (d, J = 8.1 Hz, 1 H, ArH), 6.89 (d, J = 8.7 Hz, 1 H, ArH), 7.12 (d, J = 8.7 Hz, 1 H, ArH), 7.17 (d, J = 8.1 Hz, 1 H, ArH) ppm. 13C NMR (75 MHz, CDCl3): d = 21.3 (CH3), 55.5 (OCH3), 114.4 (CH), 114.7 (CH), 117.1 (C), 120.0 (CH), 124.6 (CH), 129.1 (CH), 134.2 (C), 137.5 (C), 141.7 (C), 156.3 (C) ppm. ESI-MS: m/z (%) = 248 (6) [M + 1], 213 (18), 198 (21), 140 (35), 123 (100), 113 (24), 108 (39).
37. 2-Chloro-N-(4-methoxyphenyl)acetamide (10)37 White solid; mp 120122 C. 1H NMR (300 MHz, CDCl3): d = 3.81 (s, 3 H, OCH3), 4.19 (s, 2 H, CH2), 6.89 (d, J = 8.8 Hz, 2 H, ArH), 7.44 (d, J = 8.8 Hz, 2 H, ArH), 8.15 (s, 1 H, NH) ppm. 13C NMR (75 MHz, CDCl3): d = 42.8 (OCH3), 55.5 (CH2), 114.2 (CH), 122.0 (CH), 129.6 (C), 157.1 (C), 163.6 (C) ppm.
38. 2-(2-Chloro-5-methylphenoxy)-N-(4- methoxyphenyl)acetamide (11) White solid; mp 134136 C. 1H NMR (300 MHz, CDCl3): d = 2.35 (s, 3 H, CH3), 3.81 (s, 3 H, OCH3), 4.64 (s, 2 H, CH2), 6.78 (s, 1 H, ArH), 6.82 (d, J = 8.1 Hz, 1 H, ArH), 6.90 (d, J = 8.8 Hz, 2 H, ArH), 7.29 (d, J = 14.0 Hz, 1 H, ArH), 7.52 (d, J = 8.8 Hz, 2 H, ArH), 8.75 (s, 1 H, NH) ppm. 13C NMR (75 MHz, CDCl3): d = 21.3 (CH3), 55.5 (OCH3), 68.3 (CH2), 114.2 (CH), 115.1 (C), 119.8 (C), 121.6 (CH), 123.8 (C), 130.0 (C), 138.6 (C), 152.5 (C), 161.8 (C), 165.3 (C) ppm.
39. 4-Phenethyl-2H-benzo[b][1,4]oxazin-3 (4H)-one (9b) White solid. IR (KBr): n = 3421, 2930, 1682, 1409, 1058, 743 cm1. 1H NMR (300 MHz, CDCl3): d = 2.96 (t, J = 9.0 Hz, 2 H, CH2), 4.14 (t, J = 9.0 Hz, 2 H, CH2), 4.58 (s, 2 H, OCH2CO), 7.007.02 (m, 4 H, ArH), 7.257.34 (m, 5 H, ArH) ppm. 13C NMR (75 MHz, CDCl3): d = 33.5 (CH2), 42.7 (CH2), 67.7 (OCH2CO), 114.9 (CH), 117.4 (CH), 123.0 (CH), 124.0 (CH), 126.9 (CH), 128.5 CH), 128.7 (CH), 128.9 (CH), 138.2 (C), 145.5 (C), 164.3 (CO) ppm.