2-amino-6-nitrobenzyl alcohol synthesis
- Product Name:2-amino-6-nitrobenzyl alcohol
- CAS Number:98451-51-5
- Molecular formula:C7H8N2O3
- Molecular Weight:168.15
606-18-8
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Yield:98451-51-5 85%
Reaction Conditions:
with borane-THF in tetrahydrofuran at 0 - 30; for 1 h;Inert atmosphere;
Steps:
141 6,7-Didehydro-3-methoxy-17-methyl-8'-nitroquinolino[2',3':6,7]morphinan-14β-diol (23d)
5.1.141
6,7-Didehydro-17-methyl-8'-nitroquinolino[2',3':6,7]morphinan-3,14β-diol (29d)
Compound 29d was prepared from compound 23d according to the procedure used to prepare compound 24a.
Yield, 58%; a yellow amorphous solid.
IR (KBr): 3399, 1526, 760 cm-1. 1H NMR (300 MHz, CD3OD) δ: 1.28-1.39 (1H, m), 2.18-2.29 (2H, m), 2.40-2.49 (1H, m), 2.45 (3H, s), 2.80-3.09 (4H, m), 3.29 (1H, d, J = 18.0 Hz), 3.40 (1H, d, J = 18.0 Hz), 3.67 (1H, d, J = 17.7 Hz), 6.60 (1H, dd, J = 2.4, 8.1 Hz), 6.79 (1H, d, J = 2.4 Hz), 7.00 (1H, d, J = 8.4 Hz), 7.36 (1H, t, J = 7.8 Hz), 7.46 (1H, s), 7.68 (1H, dd, J = 1.2, 8.4 Hz), 7.81 (1H, dd, J = 1.2, 7.5 Hz).
13C NMR (75 MHz, CD3OD) δ: 25.1, 37.3, 37.5, 40.2, 41.4, 43.2, 46.7, 63.1, 70.7, 112.9, 115.2, 123.8, 125.4, 127.8, 129.3, 130.1, 131.8, 132.1, 136.5, 138.3, 142.0, 148.7, 157.1, 161.7. HRMS (ESI) Calcd for C24H24N3O4 [M+H]+: 418.1767. Found: 418.1756.
References:
Ida, Yoshihiro;Matsubara, Ayaka;Nemoto, Toru;Saito, Manabu;Hirayama, Shigeto;Fujii, Hideaki;Nagase, Hiroshi [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 19,p. 5810 - 5831]
50573-74-5
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