2-Amino-4-nitrobenzenemethanol

5.1.132 To a solution of 2-amino-4-nitrobenzoic acid (1.00 g, 5.49 mmol) in THF (20 mL) at room temperature was added BH3THF (21.96 mL, 21.96 mmol) dropwise via an addition funnel. The reaction mixture was stirred at room temperature for 12h. The reaction was then cooled in an ice bath and quenched by slow addition ofmethanol (100 mL). The mixture was concentrated and the residue was transferred toa separatory funnel containing saturated aqueous NaHCO3 solution (50 mL). The aqueous layer was extracted with ether (3 x 75 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered, and concentrated. The residue was suspended in water, filtered and dried to afford (2-amino-4-nitrophenyl)methanol (650 mg, 70percent yield) as an orange solid: ‘H NMR (400MHz, DMSO-d6) ö 7.46 (d, J=2.0 Hz, 1H), 7.38 - 7.35 (m, 2H), 5.57 (s, 2H), 5.34 (t, J5.4 Hz, 1H), 4.43 (d, J5.5 Hz, 2H).[0082] 2-Acetamido-4-nitrobenzyl alcohol (53.2 mg, 0.316 mmol) was treated with 1 mL of 6 N HCl and the reaction mixture was stirred at room temperature overnight. After neutralization with 6 N aqueous NaOH solution to pH 10, the reaction mixture was extracted with EtOAc, dried over Na2SO4, purified through flash column chromatography to give desired 2-amino-4-nitrobenzyl alcohol product (46 mg, 100percent). m.p. 178-180° C. 1H NMR (300 MHz, CDCl3) δ 7.56-7.51 (m, 2H, aromatic), 7.20 (d, 1H, J=8.1 Hz, aromatic), 4.74 (d, 2H, J=4.5 Hz), 4.52 (br s, 2H), 1.72 (t, 1H, J=4.5 Hz). MS (EI) m/z (relative intensity) 168 (M+, 100), 150 (60.8).

Molecular Weight:168.15
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:168.05349212
Monoisotopic Mass:168.05349212
Topological Polar Surface Area:92.1
Heavy Atom Count:12
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes