Thionyl Chloride → HCID 22915621, compound
Reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([NH2:20])=O)[CH:10]=[CH:9]2>>[Cl:3][C:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH3:5])[CH:7]=2)[N:12]=[C:11]([C:16]2[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=2[C:18]#[N:20])[CH:10]=1Participants
Procedure
2.5 ml (34.2 mmol) of thionyl chloride were added to 1.28 g (4.88 mmol) of 2-(6-methylquinolin-2-yl)benzamide obtained in Reference Example 7 and the mixture was stirred. After heating the mixture under reflux for 3 hours, thionyl chloride was distilled off. The residue was dissolved in 100 ml of chloroform and poured into iced water. The organic layer was separated, neutralized with 150 ml of a saturated sodium bicarbonate solution, washed with a saturated sodium chloride solution and dried over magnesium sulfate followed by filtration. The resulting filtrate was concentrated and the concentrate was subjected to silica gel chromatography using a mixed solvent of hexane and ethyl acetate (10/1) to obtain 150 mg of 2-(4-chloro-6-methylquinolin-2-yl)benzo-nitrile.
Workup
- customobtained in Reference Example 7
- temperatureAfter heating the mixture
- temperatureunder reflux for 3 hours
- distillationthionyl chloride was distilled off
- dissolutionThe residue was dissolved in 100 ml of chloroform
- additionpoured into iced water
- customThe organic layer was separated
- washwashed with a saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- filtrationfollowed by filtration
- concentrationThe resulting filtrate was concentrated
Sources & evidence
- ORD record
- ord-58dc230cc19f4c44b6a570b468de1ae5
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665881
Reaction notes
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