ChemicalBook CAS DataBase List N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE

N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE synthesis

4synthesis methods

Product Name:N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE
CAS Number:2842-44-6
Molecular formula:C10H15NO
Molecular Weight:165.23

Add reactant (0.2 mmol, 1.0 equiv), THF (2.0 mL) and CH2Br2 (0.6 mmol, 3.0 equiv) to a flame-dried 10 mL Schlenk tube in a glove box. Seal and take out of the glove box. Cool the reaction mixture to -78°C. Add nBuLi (0.56 mmol, 2.8 equiv) dropwise under N2 atmosphere within 3minutes. Stir the reaction at -78°C for 30 minutes and add ZnCl2 (0.1 mL, 0.5equiv, 1.0 M in Et2O). Allow the mixture to warm to room temperature and stir for 1 hour. Cool the mixture to 0°C. Add a premixture of H2O2 (30% in H2O, 0.5 mL) and NaOH (2.0 M, 1.0 mL). Stir the mixture at room temperature for another 1 hour and dilute with water (20 mL). Extract with DCM (30 mL x 2) and dry over Na2SO4. Filter and concentrate under vacuum. Purify the crude product by silica gel flash column chromatography to obtain product. 1H NMR (CDCl3, 500 MHz) δ 7.08 (d, J = 8.4 Hz, 2H), 6.78 (d, J = 8.4 Hz,2H), 3.80 (t, J = 5.6 Hz, 2H), 3.43 (t, J = 5.4 Hz, 2H), 2.93 (s, 3H), 2.28 (s, 3H), 2.01 (brs, 1H). 13C NMR (CDCl3, 125 MHz) δ 148.3, 129.8, 127.1, 114.0, 60.1, 56.2, 39.1, 20.4.

Fig The synthetic method of N-(2-hydroxyethyl)-N-methyl-4-toluidine

623-08-5 Synthesis

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Yield:-

Steps:

Multi-step reaction with 3 steps
1.1: 24 h / 120 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Sealed tube; Inert atmosphere
2.2: 1 h / 20 °C / Schlenk technique; Inert atmosphere
3.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; diethyl ether; water / 1 h / 0 - 20 °C / Schlenk technique; Inert atmosphere

References:

Xie, Qiqiang;Dong, Guangbin [Journal of the American Chemical Society,2021,vol. 143,# 36,p. 14422 - 14427]

623-08-5 Synthesis

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56-81-5 Synthesis