2-Chloroethanol → 1-(2-Hydroxyethyl)-4-methylquinolinium chloride

HRID 1774071Notes

Reaction equation

[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.[Cl:12][CH2:13][CH2:14][OH:15]>C(#N)C>[Cl-:12].[OH:15][CH2:14][CH2:13][N+:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution mixture of lepidine (0.8 g, 5.6 mmol) and 2-chloroethanol (2.25 g, 28 mmol) in acetonitrile (15 mL) was heated to 120° C. in a sealed tube overnight. After cooling to room temperature, the solvent was removed. The resulting mixture was precipitate from methanol and ethyl acetate to give the desired product 5 (0.79 g) in 63% yield. 1H NMR (400 MHz, DMSO-d6) δ 9.24 (d, J=6 Hz, 1H), 8.61 (d, J=7.2 Hz, 1H), 8.55 (d, J=7.2 Hz, 1H), 8.25 (m, 1H), 8.06 (m, 2H), 5.15 (br, 1H), 5.08 (t, J=4.8 Hz, 2H), 3.91 (t, J=4.8 Hz, 2H), 3.01 (s, 3H). 13C NMR (400 MHz, DMSO-d6) δ 158.8, 149.2, 137.1, 135.1, 129.7, 129.1, 127.2, 122.4, 119.5, 59.4, 59.0, 19.9. MS (FAB) m/z Calcd for C12H14NO+ 188.2 Found 188.2 [M]+.

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed

Sources & evidence

ORD record: ord-5d18dddd95214ac6a09d63e3c0f871f1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255933B2

Reaction notes

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