ChemicalBook CAS DataBase List 2-(2-aminoethyl)phenol

2-(2-aminoethyl)phenol synthesis

14synthesis methods

Product Name:2-(2-aminoethyl)phenol
CAS Number:2039-66-9
Molecular formula:C8H11NO
Molecular Weight:137.18

3156-43-2
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$60.00/5mg

2039-66-9
102 suppliers
$29.00/100mg

Yield:2039-66-9 65%

Reaction Conditions:

Stage #1: 2-(2-nitro-vinyl)-phenolwith lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 2 h;Inert atmosphere;
Stage #2: with water in tetrahydrofuran at 0;Inert atmosphere;

Steps:

4.2.1. 2-(2-Aminoethyl)phenol (3a)²⁴

A solution of 2-(2-nitrovinyl)phenol 2a (860 mg, 5.21 mmol) in THF (12 mL) was added dropwise (over 1 h) to a stirred and cooled (0 °C) suspension of LiAlH₄ (479 mg, 17.18 mmol) in THF (6 mL). Stirring was continued for 2 h at room temperature. The reaction mixture was cooled to 0 °C and then water was added. The organic solvent was removed in vacuo. The residue was dissolved in HCl (10%, 40 mL) and washed twice with EtOAc (20 mL). The combined organic layers were extracted twice with HCl (10%, 20 mL). The combined aqueous layers were treated with tartaric acid (4 equiv) and the pH was adjusted to >10 with concd NH₃ and the aqueous layers were extracted three times with chloroform (30 mL). The combined organic layers were washed with water and brine, dried over anhydrous Na₂SO₄, and evaporated. The residue was purified by chromatography on silica gel using 3-10% 2 M NH₃ in MeOH in CH₂Cl₂ to yield 3a as a white solid (464 mg, 3.38 mmol, 65%). ¹H NMR (500 MHz, CDCl₃): δ 7.12 (ddd, J=8.0, 8.0, 1.5 Hz, 1H), 6.99 (dd, J=7.5, 1.5 Hz, 1H), 6.90 (dd, J=8.0, 1.0 Hz, 1H), 6.76 (ddd, J=7.5, 7.5, 1.0 Hz, 1H), 5.40 (br, 1H), 3.09-3.07 (m, 2H), 2.80-2.78 (m, 2H).

References:

Hellal, Malik;Singh, Shambhavi;Cuny, Gregory D. [Tetrahedron,2012,vol. 68,# 6,p. 1674 - 1681] Location in patent:experimental part