2-Chloroethanol → 1-(2-Hydroxyethyl)-4-methylpyridinium chloride
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C.[Cl:8][CH2:9][CH2:10][OH:11].[C:12](#N)C>>[Cl-:8].[OH:11][CH2:10][CH2:9][N+:1]1[CH:2]=[CH:3][C:4]([CH3:12])=[CH:5][CH:6]=1Participants
4
Conditions
- Temperature
- 120 °C
Procedure
A solution mixture of picoline (0.93 g, 10 mmol) and 2-chloroethanol (4.03 g, 50 mmol) in acetonitrile (20 mL) was heated to 120° C. in a sealed tube overnight. After cooling to room temperature, the solvent was removed under vacuum. The resulting mixture was precipitate from methanol and ethyl acetate to give the desired product 9 (1.5 g) in 87% yield. 1H NMR (400 MHz, DMSO-d6) δ 8.94 (d, J=6.4 Hz, 2H), 7.98 (d, J=6.4 Hz, 2H), 5.55 (br, 1H), 4.64 (t, J=4.8 Hz, 2H), 3.81 (t, J=4.8 Hz, 2H), 2.60 (s, 3H). 13C NMR (400 MHz, DMSO-d6) δ 158.7, 144.2, 127.9, 62.1, 60.0, 21.4.
Workup
- temperatureAfter cooling to room temperature
- customthe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-3b08bd05dca7495fab49ebebb7bc905b
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403794B2
Reaction notes
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