RSC Advances
Page 8 of 36
DOI: 10.1039/C5RA07612A
Spectral characterization of the synthesized/detected compounds
Methyl N-methyl-N-nitrosoanthranilate (2) (2.0 g, 52%). Yellowish liquid; UV λmax
(CH3CN)/nm 283sh (log ɛ 4.59) and 218 (5.20); FTIR (neat) νmax/cm-1 2952.4, 1720.7, 1601.0,
1495.6, 1432.9, 1395.4, 1293.3, 1264.1, 1192.1, 1116.7, 1066.9, 1040.9, 952.6, 762.1, 711.5,
702.7; EIMS m/z 194 (M+, 1.4%), 164 (25.7, M−NO), 133 (14.6, M−OCH3−NO), 132 (100.0,
M−CH3OH−NO), 105 (19.5, M−COOCH3−NO), 104 (18.5, M−CH3OH−NO−CO), 77 (38.8,
M−C3H5N2O3); Found: C, 55.70; H, 5.22; N, 14.39; O, 24.69%. Calc. for C9H10N2O3: C, 55.67;
H, 5.19; N, 14.43; O, 24.72%; 1H and 13C NMR data, see Table 1.
Dimethyl 2,2'-(1,2-dimethylhydrazine-1,2-diyl)dibenzoate (4). EIMS m/z 328 (M+,
10.0%), 165 (63.9, M−C9H9NO2), 164 (18.2, M−C6H4(NCH3)COOCH3), 163 (22.4,
M−C9H11NO2), 148 (24.4, M−C9H11NO2−CH3), 133 (27.6, M−C9H9NO2−CH3OH), 132 (100.0,
M−C9H10NO2−CH3OH), 118 (10.3, M−C11H16NO3), 105 (69.0, M−C9H9NO2−CH3OH−CO), 104
(58.8, M−C9H9NO2−CH3−H2O−CO), 91 (12.5, M−C11H13N2O4), 77 (62.4, M−C12H15N2O4).
Methyl 5-methyl-6-oxo-(5H)-phenanthridine-4-carboxylate (5); Yellowish amorphous
solid; UV λmax (CH3CN)/nm 328 (log ɛ 4.58), 242 (5.19) and 224 (5.18); FTIR (neat) νmax/cm-1
2920.8, 2849.9, 1722.5, 1651.8, 1608.0, 1584.9, 1513.6, 1431.0, 1325.6, 1293.1, 1254.3, 1144.1,
1104.8, 1060.6, 753.3, 722.7, 691.4; Rt 36.941 min, RI (DB-5MS) 2570; EIMS m/z 267 (M+,
100.0%), 252 (25.1, M−CH3), 236 (78. 7, M−OCH3), 222 (94.0), 208 (40.6, M−COOCH3), 206
(44.4), 180 (20.7), 179 (31.2), 178 (48.0), 164 (10.2), 152 (37.8), 151 (31.2), 139 (11.8), 117
(10.0), 103 (12.6), 90 (10.6), 89 (11.6), 76 (16.3), 63 (5.9), 51 (2.3); Found: C, 71.86; H, 4.88; N,
5.27; O, 17.99%. Calc. for C16H13NO3: C, 71.90; H, 4.90; N, 5.24; O, 17.96%. 1H and 13C NMR
data, see Table 2. IR, 1H and 13C NMR spectroscopic data are in accordance with Han et al.31
Methyl N-benzoylanthranilate (6) (1.2 g, 90%). White amorphous solid; UV λmax
(CH3CN)/nm 314 (log ɛ 4.22), 267 (4.37), 234 (4.64) and 212 (4.72); FTIR (neat) νmax/cm-1
3263.9, 2949.4, 1692.5, 1666.9, 1608.4, 1589.1, 1531.3, 1494.1, 1453.7, 1432.9, 1323.3, 1295.8,
1268.0, 1251.3, 1189.7, 1178.4, 1079.9, 965.8, 896.1, 766.7, 696.4, 664.6; Rt 31.951 min, RI
(DB-5MS) 2249; EIMS m/z 255 (M+, 34.0%), 224 (2.2, M−OCH3), 196 (6.1, M−COOCH3), 105