Thionyl Chloride → 4-(1-Chloroethyl)quinoline
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11](O)[CH3:12])=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To 1-Quinolin-4-yl-ethanol (1.4 g, 8.09 mmol) in 15 ml chloroform, thiony-chloride (1.8 ml, 20.2 mmol) was added dropwise over a five minute period at room temperature. Stirring was continued for 30 minutes after which the reaction mixture was cooled to 0° C. and quenched carefully by the addition of saturated aqueous NaHCO3 (20 ml). The chloroform layer was dried over sodium sulfate, filtered and concentrated. Column purification (hexane:ethyl acetate; 1.5:3.5) gave 1.54 g (100%) of the product as a syrup which was used as such for the subsequent step.
Workup
- customquenched carefully by the addition of saturated aqueous NaHCO3 (20 ml)
- dry with materialThe chloroform layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customColumn purification (hexane:ethyl acetate; 1.5:3.5)
Sources & evidence
- ORD record
- ord-1483d4265d4e4d3298d7d1030a129870
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06294566B1
Reaction notes
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