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(2 MeO); 46.8 (C(2)); 35.6; 28.6; 21.6. Anal. calc. for C20H23NO4 (341.4): C 70.36, H 6.79, N 4.10; found: C
70.62, H 6.58, N 4.27. EI-MS: 340.8 (15, M+), 286.7 (4), 265.8 (3), 249.7 (7), 232.7 (17), 217.7 (5), 191.9 (8),
190.9 (30), 189.4 (100), 174.8 (23), 158.9 (25), 157.7 (13), 148.8 (11), 142.7 (9), 114.8 (11), 90.8 (33).
1,2,3,4-Tetrahydro-5,6-dimethoxynaphthalene-2-amine Hydrochloride (17). In a 100-ml flask were
placed Pd·C (80 mg) and 16 (1.00 g, 2.94 mmol) in MeOH (50 ml) and CHCl3 (3 ml), and a balloon filled
with H2 gas (3 l) was fitted to the flask. The mixture was deoxygenated by flushing with H2, and then
hydrogenated for 24 h at r.t. The catalyst was removed by filtration to afford 0.68 g (95%) of 17. Colorless
solid. M.p. 275–2778 (dec.; MeOH/Et2O) [lit. m.p. 270–2728 (dec. EtOH/Et2O) [6a]]. 1H-NMR (400
MHz, D2O): 6.77, 6.74 (2 AB-type d, J(7,8)=8.8 each, HÀC(7), HÀC(8)); 4.65 (br. s, NH3+, overlapping
with solvent signals); 3.64, 3.56 (2s, 2 MeO); 3.42–3.36 (m, HÀC(2)); 2.93 (AB-type dd, J(1a,1b)=16.1,
J(1a,2)=5.0, HaÀC(1)); 2.79 (AB-type dt, 2J=17.4, 3J=5.0 , HaÀC(4)); 2.65–2.54 (AB-type m, HbÀC(1),
HbÀC(4)); 2.07–2.00 (m, HaÀC(3)); 1.67–1.57 (m, HbÀC(3)). 13C-NMR (100 MHz, D2O): 150.4; 145.3;
129.3; 125.9; 125.4; 111.4; 60.2, 55.9 (2 MeO); 47.3 (C(2)); 32.3; 26.1; 21.0.
2-Amino-1,2,3,4-tetrahydronaphthalene-5,6-diol Hydrobromide (18). Prepared from 17 according to
1
[8] in 80% yield. Colorless solid. M.p. >2908 (MeOH/Et2O) (lit m.p. >3008 [6b]). H-NMR (400 MHz,
D2O): 6.58, 6.45 (2 AB-type d, J(7,8)=8.1 each, HÀC(7), HÀC(8)); 4.64 (br. s, NH3+, overlapping
with solvent and phenolic OH signals); 3.40–3.33 (m, HÀC(2)); 2.88 (AB-type dd, J(1a,1b)=15.7,
J(1a,2)=4.2, HaÀC(1)); 2.69 (AB-type dt, 2J=17.8, 3J=5.3, HaÀC(4)); 2.58 (AB-type dd,
J(1a,1b)=15.7, J(1b,2)=9.5, HbÀC(1)); 2.47 (AB-type ddd, 2J=17.8, 3J=9.9, 6.6, HbÀC(4));
2.06–1.99 (m, HaÀC(3)); 1.67–1.57 (m, HbÀC(3)). 13C-NMR (100 MHz, D2O): 142.0; 141.3; 125.0;
123.2; 121.1; 114.1; 47.4; 32.5; 26.1; 21.1.
We thank the State Planning Organization (Grade No. DPT 2004K/02) and the Atatürk University
for financial support of this work.
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Received October 28, 2005