Water → 5-Chloro-2,6-dimethoxy-4-methylquinoline
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:14][CH3:15])[CH:9]=2)[N:4]=1.S(Cl)([Cl:19])(=O)=O.O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:14][CH3:15])[C:9]=2[Cl:19])[N:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A 500 ml, four-necked round bottom flask equipped with a mechanical stirrer, condenser, thermowatch and addition funnel was charged with 2,6-dimethoxy-4-methylquinoline (9) (17.9 g, 0.09 moles) and glacial acetic acid (120 ml). The resulting solution was heated to 60° C., then a solution containing sulfuryl chloride (13.4 g, 0.01 moles) and glacial acetic acid (40 ml) was added over 20 minutes. Reaction temperature was held between 60-65° C. during this addition. The resulting solution was stirred for 1 hour at 60-65° C., then additional sulfuryl chloride (3.8 g, o,028 moles) in glacial acetic acid (10 ml) was added. The mixture was stirred an additional 30 minutes, then it was poured into 300 ml of water. The slurry was cooled to 5° C., the product removed by suction filtration, washed with water and air dried. Yield was 18.4 g (86%); mp=97-100° C.; purity by HPLC=89.7 area %.
Workup
- customA 500 ml, four-necked round bottom flask equipped with a mechanical stirrer, condenser
- additionthermowatch and addition funnel
- additionwas added over 20 minutes
- customReaction temperature
- additionwas held between 60-65° C. during this addition
- stirringThe mixture was stirred an additional 30 minutes
- temperatureThe slurry was cooled to 5° C.
- customthe product removed by suction filtration
- washwashed with water and air
- customdried
Sources & evidence
- ORD record
- ord-877aa88a373b45cfba7feb26653583ed
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479660B1
Reaction notes
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