2-(2-Hydroxyethyl)pyridine → Pyridine, 2-(2-chloroethyl)-, hydrochloride

HRID 2365389Notes

Reaction equation

HRID 2365389 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8]O.S(Cl)([Cl:12])=O>C1COCC1>[ClH:12].[Cl:12][CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

4

Reactant 2

HCID 76752-(2-Hydroxyethyl)pyridineHCID 24386Thionyl Chloride

Product 1

HCID 199467Pyridine, 2-(2-chloroethyl)-, hydrochlorideYield 52.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Pyridin-2-yl)ethanol (7.2 g, 58 mmol) and thionyl chloride (10.6 g, 89.1 mmol) were combined in THF (30 mL) and heated at reflux for 16 h. Upon cooling, the solid was filtered off and washed with THF to provide the title compound (4.2 g, 40%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.82 (d, J=5.6 Hz, 1H), 8.51-8.45 (dt, J=7.8, 1.5 Hz, 1H), 8.00 (d, J=7.9 Hz, 1H), 7.91-7.86 (m, 1H), 4.14 (t, J=6.5 Hz, 2H), 3.53 (t, J=6.5 Hz, 2H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. temperatureUpon cooling
  4. filtrationthe solid was filtered off
  5. washwashed with THF

Sources & evidence

ORD record
ord-d0cf16528cf846cbb390f0bf751e8dde
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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