Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10 Experimenteller, chemisch-präparativer Teil 282
10.4.3.17 3-Methoxy-11-methyl-11H-benzo[a]carbazol-5-carbonsäuremethylester
(119)
9
8
10
Summenformel: C20H17NO3
Molekulargewicht: 319.35
7
6b 6a
N
CH 3
6
1
CO 2CH 3
5
4a
11
10a 11a 11b
Einsatzmengen: 250 mg (778 µmol) 70
Iod
350 ml CH2Cl2
Reaktionsbedingungen: photochemisch hν, 1h
1' 1''
2
4
3
1'''
OCH 3
Aufarbeitung: säulenchromatographisch (PE / EE = 3 / 2)
Ausbeute: 13,4 mg (42 µmol; 5%)
Schmelzpunkt: 156-157°C (Essigester / Hexan)
1 H-NMR δ [ppm]:
(300 MHz) CDCl3
13 C-NMR δ [ppm]:
(75 MHz) CDCl3
4.02-4.04 (s, s, 6H, 2xCH3, 1''-H, 1'''-H); 4.29 (s, 3H, CH3,
N-CH3); 7.24-7.28 (m, 1H, CH, 8-H); 7.31-7.37 (m, 1H, CH,
9-H); 7.51 (d, 3 J=3.58, 2H, 2xCH, 2-H, 10-H); 8.13 (d,
3 J=7.63, 1H, CH, 7-H); 8.59 (d, 3 J=9.30, 1H, CH, 1-H); 8.91
(d, 4 J=2.62, 1H, CH, 4-H); 8.98 (s, 1H, CH, 6-H)
34.0 (CH3, N-CH3); 51.7 (CH3, C-1''); 55.2 (CH3, C-1''');
106.7 (CH, C-4); 109.1 (CH, C-10); 116.1 (Cq, C-5); 116.4
(Cq, C-6a); 116.9 (CH, C-2); 117.4 (Cq, C-11b); 119.4 (CH,
C-7); 120.4 (CH, C-8); 123.3 (Cq, C-6b); 123.7 (CH, C-1);
124.9 (CH, C-9); 125.9 (CH, C-6); 133.9 (Cq, C-4a); 139.0
(Cq, C-11a); 141.1 (Cq, C-10a); 157.9 (Cq, C-3); 168.4 (Cq,
C-1')
EI-MS (70 eV); m/z (%) 318.7 (_, 100.00), 287.6 (49.43), 259.9 (18.45), 148.6
(40.42), 134.6 (21.88), 106.7 (89.14), 94.7 (37.38), 80.8
(51.78), 66.7 (37.77), 55.2 (83.56)
Elementaranalyse (%): Ber.: C: 75.22 H: 5.37 N: 4.39
Gef.: C: 71.09 H: 5.70 N: 4.10