ChemicalBook CAS DataBase List 3-AMINO-N-(4-CHLOROPHENYL)BENZAMIDE

3-AMINO-N-(4-CHLOROPHENYL)BENZAMIDE synthesis

5synthesis methods

Product Name:3-AMINO-N-(4-CHLOROPHENYL)BENZAMIDE
CAS Number:115175-17-2
Molecular formula:C13H11ClN2O
Molecular Weight:246.69

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Yield:115175-17-2 97%

Reaction Conditions:

with iron⁽⁰⁾;ammonia hydrochloride in methanol; for 7 h;Reflux;

Steps:

3.1.8. General Experimental Procedures of 4ii-8ii

General procedure: To a solution of 4i-8i (3.37 mmol) in methanol (20 mL) was added: ammonium chloride (doubleamounts of 4i-8i) and iron powder (6.03 mmol) and refluxed for 7 h. The reaction mixture wasevaporated to give an oily residue, which was added with water and extracted with dichloromethane(30 mL x 3). The combined organic phase was dried with anhydrous MgSO4, filtrated, and the filtratewas evaporated to yield a crude solid, which recrystallized with ethyl acetate and n-hexane to give apure white or pale yellow solid. N-(4'-Chlorophenyl)-3-aminobenzamide (4ii). Yield: 97%; m.p.: 160-161 °C; 1H-NMR (400 MHz,DMSO-d6) δ: 5.32 (2H, s, NH2), 6.75 (1H, ddd, J = 7.9, 2.3, 1.0 Hz, H-4), 7.04 (1H, d, J = 8.0Hz,H-6), 7.08 (1H, t, J = 2.0 Hz, H-2), 7.14 (1H, t, J = 7.7 Hz, H-5), 7.38 (2H, d, J = 8.9 Hz, 3',5'), 7.80 (1H, d,J = 8.9 Hz, H-2',6'), 10.19 (1H, s, CONH); 13C-NMR (100 MHz, DMSO-d6) δ: 112.9 (C-2), 114.7 (C-6),116.9 (C-4), 121.5 (C-2',6'), 126.9 (C-5), 128.4 (C-3',5'), 129.8 (C-4'), 135.6 (C-1), 138.3 (C-1'), 148.8 (C-3),166.9 (CONH); GC-MS (EI) m/z: 246 [M]+.

References:

Lee, Soo Hyun;Lee, Wonhwa;Bae, Jong-Sup;Ma, Eunsook [Molecules,2016,vol. 21,# 5,art. no. 676]