Thionyl Chloride → 5-(1-Chloroethyl)quinoline
Reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([CH:11](O)[CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2)[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The alcohol, 1-quinolin-5-yl-ethanol (5.0 g, 28.9 mmol) in chloroform was treated with a dropwise addition of thionyl chloride (5.26 mL, 72.1 mmol) at rt. After 1 h the mixture was cooled to 0° C. and carefully quenched with a sat. solution of NaHCO3 followed by 2M NaOH until the pH was >8. The aqueous layer was extracted with chloroform and the organic fractions were combined, dried over MgSO4, filtered, and freed of solvent. The residue was purified by chromatography on SiO2 eluting with 30% ethyl acetate:hexane. The product, 5-(1-chloro-ethyl)-quinoline (Intermediate E1) was obtained as a clear oil, 4.22 g (76%).
Workup
- customcarefully quenched with a sat. solution of NaHCO3
- extractionThe aqueous layer was extracted with chloroform
- dry with materialdried over MgSO4
- filtrationfiltered
- customThe residue was purified by chromatography on SiO2 eluting with 30% ethyl acetate
Sources & evidence
- ORD record
- ord-70e57606b3484548b3398863bf487520
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838545B2
Reaction notes
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