Thionyl Chloride → 4-(Chloromethyl)quinoline
Reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1>ClCCl>[Cl:3][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Thionyl chloride (12 mL, 170 mmol) was added dropwise for 15 minutes to a solution of 4-(hydroxymethyl)quinoline (Reference Compound No. 3-1, 13 g 82 mmol) in anhydrous dichloromethane (200 mL) under ice-cooling, and the mixture was stirred for 5 hours at room temperature. The solvent was evaporated under reduced pressure, and the resulting solid was filtered off with ethyl acetate, and washed to give 17 g of mixture containing the title Reference Compound, as a yellow-white solid.
Workup
- temperaturecooling
- customThe solvent was evaporated under reduced pressure
- filtrationthe resulting solid was filtered off with ethyl acetate
- washwashed
Sources & evidence
- ORD record
- ord-f614f3fcbaa94baf972edb94ac8cefc1
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897774B2
Reaction notes
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