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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 183, 2008 - Issue 6
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Original Articles

Simple and High Yielding Synthesis of New α-Aminophosphonates from Imines

Rajkumar U. Pokalwar Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, India
,
Rajkumar V. Hangarge Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, India
,
Balaji R. Madje Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, India
,
Madhav N. Ware Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, India
&
Murlidhar S. Shingare Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, India
Pages 1461-1470 | Received 04 Jul 2007, Accepted 20 Jul 2007, Published online: 04 Jun 2008

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  • Spectral data for the all the compounds are as given as follows. 3a) Diethyl (3- fluorophenylamino)(2-chloroquinolin-3-yl)methylphosphonate: IR (KBr): 3311 cm-1 (-NH); 1234 cm-1 (─P═O); 1032 cm−1(─P─O─C) 1 H NMR (CDCl 3 , δ ppm): 1.05 (t, 3H, O─CH2─CH 3, J = 8 Hz); 1.35 (t, 3H, O─CH2─CH 3,J = 8 Hz); 3.7 (m, 1H, O─CH 2─CH3); 3.9 (m, 1H, O─CH 2─CH3); 4.2 (m, 2H, O─CH 2─CH3); 5.4 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.3–6.5 (m, 3H, Ph-H, C2,C4, C6); 7.0 (dd, 1H, Ph─H, C5,J = 8 Hz); 7.5 (t, 1H, Quinolin-H, C5,J = 8 Hz); 7.69 (t, 1H, Quinolin-H, C6,J = 8 Hz); 7.75 (d,1H, Quinolin-H, C7,J = 8 Hz); 7.99 (d, 1H, Quinolin-H, C8,J = 8 Hz); 8.34 (d, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 423.1 (m+1) and 425.1 (m+3). Elemental analysis: C20H21ClFN2O3P Calcd.: C: 56.81%, H: 5.01%, N: 6.63%; Found: C: 56.72%, H: 4.95%, N: 6.65%. 3b) Diethyl (3-fluorophenylamino)(2-chloro-6-methylquinolin-3-yl)methylphosphonate: IR (KBr): 3305 cm−1 (─NH); 1230 cm−1 (═P═O); 1022 cm−1(─P─O─C) 1 H NMR (CDCl 3 , δ ppm): 1.05 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.38 (t, 3H, O─CH2─CH 3,J = 8 Hz); 2.48 (s, 3H, Quinolin-CH 3); 3.68 (m, 1H, O─CH 2─CH3); 3.88 (m, 1H, O─CH 2─CH3); 4.22 (m, 2H, O─CH 2─CH3); 5.16 (s, 1H, ─CH─NH─Ph); 5.35 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.28–6.42 (m, 3H, Ph─H, C2,C4, C6); 7.02 (dd, 1H, Ph─H, C5,J = 8 Hz); 7.5 (d, 1H, Quinolin-H, C7,J = 8 Hz); 7.6 (s, 1H, Quinolin-H, C5); 7.9 (d,1H, Quinolin-H, C8,J = 8 Hz); 8.3 (d, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 437.1 (m+1) and 439.2 (m+3). Elemental analysis: C21H23ClFN2O3P Calcd.: C: 57.74%, H: 5.31%, N: 6.41%; Found: C: 57.62%, H: 5.21%, N: 6.35%. 3c) Diethyl (3-fluorophenylamino)(2-chloro-7-methylquinolin-3-yl)methylphosphonate: IR (KBr): 3296 cm−1 (─NH); 1230 cm−1 (─P═O); 1033 cm−1(─P─O─C) 1 H NMR (CDCl 3 , δ ppm): 1.03 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.36 (t, 3H, O─CH2─CH 3,J = 8 Hz); 2.54 (s, 3H, Quinolin-CH 3); 3.66 (m, 1H, O─CH 2─CH3); 3.89 (m, 1H, O─CH 2-CH3); 4.22 (m, 2H, O─CH 2─CH3); 5.15 (s, 1H, ─CH─NH─Ph); 5.35 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.28–6.5 (m, 3H, Ph─H, C2,C4, C6); 7.0 (dd, 1H, Ph─H, C5,J = 8 Hz); 7.34 (d, 1H, Quinolin-H, C6,J = 4 Hz); 7.65 (d, 1H, Quinolin-H, C5,J = 8 Hz); 7.77 (s, 1H, Quinolin-H, C8); 8.27 (d, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 437.0 (m+1) and 439.1 (m+3). Elemental analysis: C21H23ClFN2O3P Calcd.: C: 57.74%, H: 5.31%, N: 6.41%; Found: C: 57.50%, H: 5.15%, N: 6.30%. 3d) Diethyl (3-fluorophenylamino)(2-chloro-8-methylquinolin-3-yl) methylphosphonate: IR (KBr): 3296 cm−1 (─NH); 1235 cm−1 (─ P═O); 1028 cm−1(─P─O─C) 1 H NMR (CDCl 3 , δ ppm): 1.05 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.36 (t, 3H, O─CH2─CH 3,J = 8 Hz); 2.5 (s, 3H, Quinolin─CH 3); 3.68 (m, 1H, O─CH 2─CH3); 3.9 (m, 1H, O─CH 2─CH3); 4.22 (m, 2H, O─CH 2─CH3); 5.18 (s, 1H, ─CH─NH─Ph); 5.35 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.2–6.5 (m, 3H, Ph─H, C2,C4, C6); 7.0 (dd, 1H, Ph─H, C5,J = 8 Hz); 7.33 (t, 1H, Quinolin-H, C6,J = 8 Hz); 7.5 (d, 1H, Quinolin-H, C7,J = 4 Hz); 7.6 (d, 1H, Quinolin-H, C5,J = 8 Hz); 8.22 (s, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 437.2 (m+1) and 439.1 (m+3). Elemental analysis: C21H23ClFN2O3P Calcd.: C: 57.74%, H: 5.31%, N: 6.41%; Found: C: 57.65%, H: 5.25%, N: 6.40%. 3e) Diethyl (3-fluorophenylamino)(2-chloro-6-methoxyquinolin-3-yl) methylphosphonate: IR (KBr): 3305 cm−1 (─ NH); 1224 cm−1 (─ P═O); 1033 cm−1(─P─O─C) 1 H NMR (CDCl 3, δ ppm): 1.05 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.35 (t, 3H, O─CH2─CH 3,J = 8 Hz); 3.68 (m, 1H, O─CH 2-CH3); 3.88 (s, 3H, Quinolin─O─CH 3); 3.9 (m, 1H, O─CH 2─CH3); 4.22 (m, 2H, O─CH 2─CH3); 5.16 (s, 1H, ─CH─NH─Ph); 5.35 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.28–6.5 (m, 3H, Ph-H, C2,C4, C6);; 6.9 (s, 1H, Quinolin-H, C5); 7.0 (dd, 1H, Ph-H, C5, J = 8 Hz); 7.33 (d, 1H, Quinolin-H, C7,J = 8 Hz); 7.88 (d, 1H, Quinolin-H, C8,J = 8 Hz); 8.22 (d, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 453.1 (m+1) and 455.1 (m+3). Elemental analysis: C21H23ClFN2O4P Calcd.: C: 55.70%, H: 5.12%, N: 6.19%; Found: C: 55.52%, H: 4.90%, N: 6.05%. 3f) Diethyl (3-fluorophenylamino)(2-chloro-7-methoxyquinolin-3-yl) methylphosphonate: IR (KBr): 3296 cm−1 (─ NH); 1230 cm−1 (─ P═O); 1024 cm−1(─P─O─C) 1 H NMR (CDCl 3 , δ ppm): 1.05 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.33 (t, 3H, O─CH2─CH 3,J = 8 Hz); 3.68 (m, 1H, O─CH 2─CH3); 3.86 (s, 3H, Quinolin─O─CH 3); 3.9 (m, 1H, O-CH 2─CH3); 4.22 (m, 2H, O─CH 2─CH3); 5.16 (s, 1H, -CH-NH-Ph); 5.32 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.3–6.5 (m, 3H, Ph-H, C2, C4,C6); 7.0 (dd, 1H, Ph─H, C5,J = 8 Hz); 7.2 (d, 1H, Quinolin-H, C6,J = 8 Hz); 7.3 (s, 1H, Quinolin-H, C8); 7.62 (d,1H, Quinolin-H, C5,J = 8 Hz); 8.22 (d, 1H, Quinolin-H, C4, J = 8 Hz). ES-MS: m/z 453.1 (m+1) and 455.0 (m+3). Elemental analysis: C21H23ClFN2O4P Calcd.: C: 55.70%, H: 5.12%, N: 6.19%; Found: C: 55.62%, H: 5.02%, N: 6.10%. 3g) Diethyl (3-fluorophenylamino) (2-chloro-6-ethoxyquinolin-3-yl) methylphosphonate: IR (KBr): 3302 cm−1 (─ NH); 1232 cm−1 (─ P═O); 1035 cm−1(─P─O─C) 1 H NMR (CDCl 3 , δ ppm): 1.03 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.35 (t, 3H, O─CH2-CH 3,J = 8 Hz); 1.45 (t, 3H, Quinolin─O─CH2─CH 3,J = 4 Hz); 3.66 (m, 1H, O─CH 2─CH3); 3.89 (m, 1H, O─CH 2-CH3); 4.06 (m, 2H, Quinolin─O─CH 2─CH3); 4.22 (m, 2H, O─CH 2-CH3); 5.34 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.28–6.5 (m, 3H, Ph-H, C2, C4,C6); 6.99 (d,1H, Quinolin-H, C5,J = 8 Hz); 7.02 (dd, 1H, Ph-H, C5,J = 8 Hz); 7.32 (d, 1H, Quinolin-H, C7,J = 4 Hz); 7.87 (d,1H, Quinolin-H, C8,J = 8 Hz); 8.2 (s, 1H, Quinolin-H, C4,J = 4 Hz). ES-MS: m/z 467.2 (m+1) and 469.2 (m+3). Elemental analysis: C22H25ClFN2O4P Calcd.: C: 56.60%, H: 5.40%, N: 6.00%; Found: C: 56.72%, H: 5.30%, N: 6.02%. 3h) Diethyl (3-fluorophenylamino) (2-chloro-8-ethylquinolin-3-yl) methylphosphonate: IR (KBr): 3297 cm−1 (─ NH); 1237 cm−1 (─P═O); 1028 cm−1(─P─O─C) 1 H NMR (CDCl 3 , δ ppm): 1.04 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.35 (t, 3H, O─CH2─CH 3, J = 7 Hz); 1.38 (t, 3H, Quinolin─CH2─CH 3,J = 8 Hz); 3.22 (m, 2H, Quinolin ─CH 2─CH3); 3.7 (m, 1H, O─CH 2─CH3); 3.9 (m, 1H, O─CH 2─CH3); 4.2 (m, 2H, O─CH 2─CH3); 5.37 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.28–6.40 (m, 3H, Ph─H, C2,C4, C6); 7.02 (dd, 1H, Ph─H, C5,J = 8 Hz); 7.42 (t, 1H, Quinolin-H, C6,J = 8 Hz); 7.54 (d, 1H, Quinolin-H, C7, J = 8 Hz; 7.59 (d,1H, Quinolin-H, C5,J = 8 Hz); 8.28 (d, 1H, Quinolin-H, C4,J = 4 Hz). ES-MS: m/z 451.3 (m+1) and 453.2 (m+3). Elemental analysis: C22H25ClFN2O3P Calcd.: C: 58.61%, H: 5.59%, N: 6.21%; Found: C: 58.52%, H: 5.46%, N: 6.12%. 3i) Diethyl (o -tolylamino) (2-chloroquinolin-3-yl) methylphosphonate: IR (KBr): 3395 cm−1 (─ NH); 1236 cm−1 (─ P═O); 1024 cm−1(─P─O─C) 1 H NMR (CDCl 3 , δ ppm): 1.0 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.3 (t, 3H, O─CH2─CH 3, J = 8 Hz); 2.3 (s, 3H, Ph─CH 3,); 3.7 (m, 1H, O─CH 2-CH3); 3.9 (m, 1H, O─CH 2─CH3); 4.2 (m, 2H, O─CH 2-CH3); 4.9 (s, 1H, ─CH─NH─Ph); 5.4 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.4 (d, 1H, Ph─H, C6); 6.6 (t, 1H, Ph─H, C4); 6.9 (t, 1H, Ph─H, C5,J = 8 Hz); 7.0 (d, 1H, Ph─H, C3,J = 8 Hz); 7.5 (t, 1H, Quinolin─H, C6,J = 8 Hz); 7.7 (t, 1H, Quinolin-H, C7,J = 8 Hz); 7.8 (d,1H, Quinolin-H, C5); 8.0 (d, 1H, Quinolin-H, C8,J = 8 Hz); 8.3 (d, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 419.1 (m+1) and 421.1 (m+3). Elemental analysis: C21H24ClN2O3P Calcd.: C: 60.22%, H: 5.78%, N: 6.69%; Found: C: 60.12%, H: 5.65%, N: 6.61%. 3j) Diethyl (o -tolylamino) (2-chloro-6-methylquinolin-3-yl) methylphosphonate: IR (KBr): 3392 cm−1 (─NH); 1232 cm−1 (─P═O); 1033 cm−1 (─P─O─C) 1 H NMR (CDCl 3,δ ppm): 1.1 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.3 (t, 3H, O─CH2─CH 3,J = 8 Hz); 2.3 (s, 3H, Ph─CH 3,); 2.5 (s, 3H, Quinolin─CH 3,); 3.7 (m, 1H, O─CH 2─CH3); 3.9 (m, 1H, O─CH 2─CH3); 4.2 (m, 2H, O─CH 2─CH3); 4.88 (s, 1H, ─CH─NH─Ph); 5.38 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.4 (d, 1H, Ph─H, C6,J = 8 Hz); 6.6 (t, 1H, Ph─H, C4,J = 8 Hz); 6.9 (t, 1H, Ph─H, C5); 7.0 (d, 1H, Ph─H, C3); 7.5 (d, 1H, Quinolin-H, C7,J = 8 Hz); 7.55 (s, 1H, Quinolin-H, C5); 7.9 (d,1H, Quinolin-H, C8,J = 8 Hz); 8.3 (s, 1H, Quinolin-H, C4). ES-MS: m/z 433.2 (m+1) and 435.1 (m+3). Elemental analysis: C22H26ClN2O3P Calcd.: C: 61.04%, H: 6.05%, N: 6.47%; Found: C: 60.92%, H: 5.94%, N: 6.35%. 3k) Diethyl ( o -tolylamino) (2-chloro-7-methylquinolin-3-yl) methylphosphonate: IR (KBr): 3354 cm−1(─NH); 1235 cm−1 (─P═O); 1035 cm−1 (─P─O─C) 1 H NMR (CDCl 3, δ ppm): 1.05 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.35 (t, 3H, O─CH2─CH 3,J = 8 Hz); 2.33 (s, 3H, Ph─CH 3,); 2.52 (s, 3H, Quinolin-CH 3,); 3.73 (m, 1H, O─CH 2─CH3); 3.94 (m, 1H, O─CH 2-CH3); 4.26 (m, 2H, O─CH 2─CH3); 4.92 (s, 1H, ─CH─NH-Ph); 5.49 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.36 (d, 1H, Ph─H, C6,J = 8 Hz); 6.63 (t, 1H, Ph─H, C4,J = 8 Hz); 6.94 (t, 1H, Ph─H, C5,J = 8 Hz); 7.04 (d, 1H, Ph─H, C3,J = 8 Hz); 7.33 (d, 1H, Quinolin-H, C6,J = 8 Hz); 7.64 (d, 1H, Quinolin-H, C5,J = 8 Hz); 7.76 (s,1H, Quinolin-H, C8); 8.26 (s, 1H, Quinolin-H, C4). ES-MS: m/z 433.3 (m+1) and 435.2 (m+3). Elemental analysis: C22H26ClN2O3P Calcd.: C: 61.04%, H: 6.05%, N: 6.47%; Found: C: 60.86%, H: 5.90%, N: 6.30%. 3l) Diethyl ( o -tolylamino) (2-chloro-8-methylquinolin-3-yl) methylphosphonate: IR (KBr): 3418 cm−1 (─NH); 1238 cm−1 (─P═O); 1024 cm−1 (─P─O─C) 1 H NMR (CDCl 3 ,δ ppm): 1.0 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.3 (t, 3H, O─CH2─CH 3,J = 8 Hz); 2.3 (s, 3H, Ph─CH 3,); 3.7 (m, 1H, O─CH 2─CH3); 3.9 (m, 1H, O─CH 2-CH3); 4.2 (m, 2H, O─CH 2─CH3); 4.88 (s, 1H, ─CH─NH-Ph); 5.3 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.4 (d, 1H, Ph-H, C6,J = 8 Hz); 6.6 (d, 1H, Ph─H, C4,J = 8 Hz); 6.9 (t, 1H, Ph─H, C5); 7.0 (d, 1H, Ph─H, C3,J = 8 Hz); 7.3 (t, 1H, Quinolin-H, C6); 7.4 (d, 1H, Quinolin-H, C7); 7.6 (d,1H, Quinolin-H, C5); 8.22 (d, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 433.3 (m+1) and 435.2 (m+3). Elemental analysis: C22H26ClN2O3P Calcd.: C: 61.04%, H: 6.05%, N: 6.47%; Found: C: 60.96%, H: 5.99%, N: 6.40%. 3m) Diethyl ( o -tolylamino) (2-chloro-6-methoxyquinolin-3-yl) methylphosphonate: IR (KBr): 3341 cm−1 (-NH); 1237 cm−1 (─P═O); 1032 cm−1 (─P─O─C) 1 H NMR (CDCl 3 ,δ ppm): 1.05 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.35 (t, 3H, O─CH2─CH 3,J = 8 Hz); 2.34 (s, 3H, Ph─CH 3,); 3.69 (m, 1H, O─CH 2─CH3); 3.87 (s, 3H, Quinolin─O ─CH 3); 4.0 (m, 1H, O─CH 2─CH3); 4.22 (m, 2H, O─CH 2─CH3); 5.4 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.35 (d, 1H, Ph─H, C6,J = 8 Hz); 6.63 (t, 1H, Ph─H, C4,J = 8 Hz); 6.94 (t, 1H, Ph─H, C5,J = 8 Hz); 7.0 (s, 1H, Quinolin─H, C5,J = 4 Hz); 7.05 (d, 1H, Ph─H, C3,J = 8 Hz); 7.31 (d, 1H, Quinolin-H, C7,J = 4 Hz); 7.87 (d,1H, Quinolin-H, C8,J = 8 Hz); 8.21 (d, 1H, Quinolin-H, C4,J = 4 Hz). ES-MS: m/z 449.2 (m+1) and 451.1 (m+3). Elemental analysis: C22H26ClN2O4P Calcd.: C: 58.86%, H: 5.84%, N: 6.24%; Found: C: 58.72%, H: 5.72%, N: 6.15%. 3n) Diethyl ( o -tolylamino)(2-chloro-7-methoxyquinolin-3-yl) methylphosphonate: IR (KBr): 3386 cm-1 (─NH); 1236 cm-1 (─P═O); 1026 cm-1 (─P─O─C) 1 H NMR (CDCl3,δ ppm): 1.06 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.33 (t, 3H, O─CH2─CH 3,J = 8 Hz); 2.3 (s, 3H, Ph─CH 3,); 3.7 (m, 1H, O─CH 2─CH3); 3.85 (s, 3H, Quinolin─O ─CH 3); 3.92 (m, 1H, O─CH 2─CH3); 4.22 (m, 2H, O─CH 2─CH3); 4.88 (s, 1H, ─CH─NH─Ph); 5.38 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.4 (d, 1H, Ph─H, C6,J = 8 Hz); 6.6 (t, 1H, Ph─H, C4,J = 8 Hz); 6.9 (t, 1H, Ph─H, C5,J = 4 Hz); 7.0 (d, 1H, Ph─H, C3,J = 8 Hz); 7.2 (d, 1H, Quinolin─H, C6,J = 8 Hz);7.3 (s, 1H, Quinolin-H, C8); 7.6 (d,1H, Quinolin-H, C5); 8.2 (d, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 449.0 (m+1) and 451.1 (m+3). Elemental analysis: C22H26ClN2O4P Calcd.: C: 58.86%, H: 5.84%, N: 6.24%; Found: C: 58.79%, H: 5.76%, N: 6.10%. 3o) Diethyl ( o -tolylamino) (2-chloro-6-ethoxyquinolin-3-yl) methylphosphonate: IR (KBr): 3341 cm-1 (─NH); 1237 cm-1 (─P═O); 1032 cm-1 (─P─O─C) 1 H NMR (CDCl3,δ ppm): 1.05 (t, 3H, O─CH2-CH 3,J = 8 Hz); 1.35 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.44 (t, 3H, Quinolin─O─CH2─CH 3,J = 8 Hz); 2.33 (s, 3H, Ph─CH 3,); 3.7 (m, 1H, O─CH 2─CH3); 3.9 (m, 1H, O-CH 2─CH3); 4.05 (q, 2H, Quinolin─O─CH 2─CH3); 4.22 (m, 2H, O─CH 2─CH3); 5.39 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.36 (d, 1H, Ph─H, C6,J = 8 Hz); 6.63 (t, 1H, Ph─H, C4,J = 8 Hz); 6.94 (t, 1H, Ph─H, C5,J = 8 Hz); 6.96 (d, 1H, Quinolin-H, C5, J = 4 Hz); 7.05 (d, 1H, Ph─H, C3,J = 8 Hz); 7.33 (d, 1H, Quinolin─H, C7.J = 8 Hz); 7.86 (d,1H, Quinolin-H, C8,J = 8 Hz); 8.2 (d, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 463.3 (m+1) and 465.3 (m+3). Elemental analysis: C23H28ClN2O4P Calcd.: C: 59.68%, H: 6.10%, N: 6.05%; Found: C: 59.72%, H: 5.96%, N: 6.00%. 3p) Diethyl ( o -tolylamino) (2-chloro-8-ethylquinolin-3-yl) methylphosphonate: IR (KBr): 3323 cm−1 (─ NH); 1238 cm−1 (─P═O); 1030 cm−1(─P─O─C) 1 H NMR (CDCl 3 ,δ ppm): 1.06 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.32 (t, 3H, O─CH2─CH 3,J = 8 Hz); 1.4 (t, 3H, Quinolin─CH2─CH 3, J = 8 Hz); 2.34 (s, 3H, Ph─CH 3,); 3.2 (q, 2H, Quinolin -CH 2-CH3); 3.7 (m, 1H, O─CH 2─CH3); 3.9 (m, 1H, O─CH 2─CH3); 4.2 (m, 2H, O─CH 2─CH3); 4.9 (s, 1H, ─CH─NH-Ph); 5.36 (d, 1H, ─NH─CH─P═O, J = 24 Hz); 6.4 (d, 1H, Ph-H, C6,J = 8 Hz); 6.6 (t, 1H, Ph─H, C4,J = 8 Hz); 6.9 (t, 1H, Ph─H, C5,J = 4 Hz); 7.04 (d, 1H, Ph─H, C3,J = 8 Hz); 7.42 (t,1H, Quinolin-H, C6,J = 8 Hz); 7.5 (d, 1H, Quinolin-H, C7.J = 8 Hz); 7.67 (d, 1H, Quinolin-H, C5,J = 8 Hz); 8.3 (d, 1H, Quinolin-H, C4,J = 8 Hz). ES-MS: m/z 447.1 (m+1) and 449.2 (m+3). Elemental analysis: C23H28ClN2O3P Calcd.: C: 61.81%, H: 6.32%, N: 6.27%; Found: C: 61.70%, H: 6.21%, N: 6.18%
  • Meth-Cohn , O. , Narine , B. and Tarnowski , B. 1981 . J. Chem. Soc., Perkin Trans-1 , : 1520

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