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

HRID 1774074Notes

Reaction equation

HRID 1774074 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]=1

Participants

4

Reactant 3

HCID 342-ChloroethanolHCID 6342AcetonitrileHCID 79752-Methylpyridine

Product 1

HCID 133080101-(2-Hydroxyethyl)-4-methylpyridinium chlorideYield 87%

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).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d857f3909cc84ac4b1d3601b9c1d86bf
Source dataset
uspto-grants-2016_02
Patent number
US09255933B2

Reaction notes

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